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13734-34-4

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13734-34-4 Usage

Chemical Properties

N-(tert-Butoxycarbonyl)-L-phenylalanine is white fine crystalline powder

Uses

Different sources of media describe the Uses of 13734-34-4 differently. You can refer to the following data:
1. N-(tert-Butoxycarbonyl)-L-phenylalanine is used in enantioselective hydrolysis of amino acid esters. Acts as an inhibitor of gastric acid secretion.
2. N-Boc-L-phenylalanine is a derivative of Phenylalanine used in enantioselective hydrolysis of amino acid esters.

Preparation

Sodium hydroxide (4.4 g, 0.11 mol) was placed in a flask, and dissolved in water (110 mL). Phenylalanine (16.5 g, 0.1 mol) was added, the suspension was stirred until a solution was obtained, and then tert-butanol (75 mL) was added. Boc2O (22.3 g, 0.12 mol) was then added with stirring over a period of 1 h, keeping the mixture near 0 ℃. A white precipitate was produced, and at the end of the addition the pH had dropped to 7.5–8.5. The mixture was then carefully acidified by the slow, continuous addition of saturated citric acid to give the product N-tert-butoxycarbonyl-L-phenylalanine (21.5 g, 81%); mp 85℃; [a]21D = t25:5 (c = 1, ethanol).

Check Digit Verification of cas no

The CAS Registry Mumber 13734-34-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,3,7,3 and 4 respectively; the second part has 2 digits, 3 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 13734-34:
(7*1)+(6*3)+(5*7)+(4*3)+(3*4)+(2*3)+(1*4)=94
94 % 10 = 4
So 13734-34-4 is a valid CAS Registry Number.
InChI:InChI=1/C14H19NO4/c1-14(2,3)19-13(18)15-11(12(16)17)9-10-7-5-4-6-8-10/h4-8,11H,9H2,1-3H3,(H,15,18)(H,16,17)/p-1/t11-/m0/s1

13734-34-4 Well-known Company Product Price

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  • TCI America

  • (B1332)  N-(tert-Butoxycarbonyl)-L-phenylalanine  >99.0%(T)

  • 13734-34-4

  • 5g

  • 191.00CNY

  • Detail
  • TCI America

  • (B1332)  N-(tert-Butoxycarbonyl)-L-phenylalanine  >99.0%(T)

  • 13734-34-4

  • 25g

  • 496.00CNY

  • Detail
  • Alfa Aesar

  • (A16017)  N-Boc-L-phenylalanine, 99%   

  • 13734-34-4

  • 5g

  • 370.0CNY

  • Detail
  • Alfa Aesar

  • (A16017)  N-Boc-L-phenylalanine, 99%   

  • 13734-34-4

  • 25g

  • 1605.0CNY

  • Detail
  • Aldrich

  • (15480)  Boc-Phe-OH  ≥99.0% (T)

  • 13734-34-4

  • 15480-5G

  • 417.69CNY

  • Detail
  • Aldrich

  • (15480)  Boc-Phe-OH  ≥99.0% (T)

  • 13734-34-4

  • 15480-25G

  • 996.84CNY

  • Detail
  • Aldrich

  • (15480)  Boc-Phe-OH  ≥99.0% (T)

  • 13734-34-4

  • 15480-100G

  • 2,322.45CNY

  • Detail

13734-34-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name N-(tert-Butoxycarbonyl)-L-phenylalanine

1.2 Other means of identification

Product number -
Other names Boc-L-Phenylalanine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:13734-34-4 SDS

13734-34-4Synthetic route

L-phenylalanine
63-91-2

L-phenylalanine

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

Conditions
ConditionsYield
With sodium hydroxide In 1,4-dioxane at 0 - 20℃; for 3.5h;100%
Stage #1: L-phenylalanine With sodium hydroxide In 1,4-dioxane; water at 0℃; for 0.25h;
Stage #2: di-tert-butyl dicarbonate In 1,4-dioxane; water at 0 - 20℃;
100%
With sodium hydrogencarbonate; sodium hydroxide In 1,4-dioxane; water at 20℃; for 23h; Cooling with ice; Inert atmosphere;100%
L-phenylalanine
63-91-2

L-phenylalanine

2-t-butoxycarbonyloxy-3,6-diisopropylpyrazine
104272-92-6

2-t-butoxycarbonyloxy-3,6-diisopropylpyrazine

N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

Conditions
ConditionsYield
With triethylamine In water; acetonitrile for 24h; Ambient temperature;100%
2-tert-butoxycarbonylamino-3-phenylpropionic acid allyl ester
160788-63-6

2-tert-butoxycarbonylamino-3-phenylpropionic acid allyl ester

N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

Conditions
ConditionsYield
With pyrrolidine; resin-plug bound Pd In tetrahydrofuran for 24h; Heating;100%
With formic acid; triethylamine In acetonitrile at 80℃; for 4h; Inert atmosphere;82%
(S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester
51987-73-6

(S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester

N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

Conditions
ConditionsYield
Stage #1: (S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester With dimethylsulfoxonium methylide In tetrahydrofuran at 20℃; for 0.333333h; Inert atmosphere;
Stage #2: With potassium hydrogensulfate; water In ethyl acetate pH=3; Inert atmosphere;
99%
Stage #1: (S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 1h;
Stage #2: With sodium hydroxide; water In tetrahydrofuran
98%
With sodium hydroxide In methanol
C20H31NO4S2

C20H31NO4S2

N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene; 2-hydroxyethanethiol at 20 - 25℃; for 0.166667h; Reagent/catalyst; Time;99%
(S)-N-tert-butoxycarbonyl-2-amino-3-phenylpropanol
66605-57-0

(S)-N-tert-butoxycarbonyl-2-amino-3-phenylpropanol

N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

Conditions
ConditionsYield
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; trichloroisocyanuric acid; sodium hydrogencarbonate; sodium bromide In water; acetone at 20℃; for 6h;98%
With dipyridinium dichromate In N,N-dimethyl-formamide for 24h;81%
Stage #1: (S)-N-tert-butoxycarbonyl-2-amino-3-phenylpropanol With Dess-Martin periodane In dichloromethane at 20℃; for 1.5h;
Stage #2: With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene In tetrahydrofuran; water; tert-butyl alcohol for 1.5h;
(S)-(1,1-dioxido-4-oxo-3-phenyl-4H-thiochromen-2-yl)methyl 2-((tert-butoxycarbonyl)amino)-3-phenylpropanoate

(S)-(1,1-dioxido-4-oxo-3-phenyl-4H-thiochromen-2-yl)methyl 2-((tert-butoxycarbonyl)amino)-3-phenylpropanoate

A

C16H10O3S
1033736-87-6

C16H10O3S

B

N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

Conditions
ConditionsYield
In chloroform-d1 for 0.233333h; Solvent; Photolysis; Inert atmosphere;A n/a
B 98%
{(R)-1-[((1S,2S)-2-Hydroxy-1-methyl-2-phenyl-ethyl)-methyl-carbamoyl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester
185509-03-9

{(R)-1-[((1S,2S)-2-Hydroxy-1-methyl-2-phenyl-ethyl)-methyl-carbamoyl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester

A

N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

B

Boc-D-Phe-OH
18942-49-9

Boc-D-Phe-OH

Conditions
ConditionsYield
With tetra(n-butyl)ammonium hydroxide In water; tert-butyl alcohol for 2.5h; Heating; Yields of byproduct given. Title compound not separated from byproducts;A n/a
B 97%
L-phenylalanine
63-91-2

L-phenylalanine

N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

Conditions
ConditionsYield
With triethylamine In water; N,N-dimethyl-formamide for 12h; Ambient temperature;96%
tert-butyl pyridin-2-yl carbonate
89985-91-1

tert-butyl pyridin-2-yl carbonate

L-phenylalanine, dicyclohexylammonium salt

L-phenylalanine, dicyclohexylammonium salt

A

2-hydroxypyridin
142-08-5

2-hydroxypyridin

B

N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

Conditions
ConditionsYield
With triethylamine In water; N,N-dimethyl-formamide for 12h; Ambient temperature;A n/a
B 96%
L-phenylalanine
63-91-2

L-phenylalanine

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile
58632-95-4

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile

N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

Conditions
ConditionsYield
With triethylamine In 1,4-dioxane; water for 3h;95%
With triethylamine In 1,4-dioxane; water for 4h; Ambient temperature;
In acetonitrile at 25℃; for 12h;
L-phenylalanine
63-91-2

L-phenylalanine

tert-butyl 1H-benzo[d][1,2,3]triazole-1-carboxylate
130384-98-4

tert-butyl 1H-benzo[d][1,2,3]triazole-1-carboxylate

N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

Conditions
ConditionsYield
With sodium hydroxide In 1,4-dioxane for 24h; Ambient temperature;95%
L-phenylalanine
63-91-2

L-phenylalanine

tert-butyl (2,4-dioxo-3-azaspiro[5,5]undecan-3-yl) carbonate

tert-butyl (2,4-dioxo-3-azaspiro[5,5]undecan-3-yl) carbonate

N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

Conditions
ConditionsYield
With sodium carbonate In water; acetone at 25℃; for 9h; Temperature;95%
L-phenylalanine
63-91-2

L-phenylalanine

tert-butyl 2-oxo-1,3-oxazole-3(2H)-carboxylate
75844-68-7

tert-butyl 2-oxo-1,3-oxazole-3(2H)-carboxylate

N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

Conditions
ConditionsYield
With dmap In water; acetone Ambient temperature;93%
With dmap In 1,4-dioxane; water for 15h; Ambient temperature;93%
L-phenylalanine
63-91-2

L-phenylalanine

(N-hydroxy-5-norbornene-2,3-diformylimino)tert-butyl ester
64205-15-8

(N-hydroxy-5-norbornene-2,3-diformylimino)tert-butyl ester

N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

Conditions
ConditionsYield
With tertiary amine In 1,4-dioxane; water for 3h;91%
tert-butyldicarbonate
34619-03-9

tert-butyldicarbonate

L-phenylalanine
63-91-2

L-phenylalanine

N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

Conditions
ConditionsYield
With sodium hydroxide In water; tert-butyl alcohol for 13h; Inert atmosphere;91%
N-(tert-butoxycarbonyl)-L-phenylalanine benzyl ester
66617-58-1

N-(tert-butoxycarbonyl)-L-phenylalanine benzyl ester

N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

Conditions
ConditionsYield
With formic acid; potassium hydroxide In ethanol at 70℃; for 1h;91%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

Conditions
ConditionsYield
With sodium hydrogencarbonate In ethanol for 3h; sonication;90%
2-tert-butoxycarbonylamino-3-phenyl-propionic acid 2-(2,5-dimethyl-phenyl)-2-oxo-ethyl ester

2-tert-butoxycarbonylamino-3-phenyl-propionic acid 2-(2,5-dimethyl-phenyl)-2-oxo-ethyl ester

A

2,3-dihydro-6-methyl-1H-inden-1-one
24623-20-9

2,3-dihydro-6-methyl-1H-inden-1-one

B

N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

Conditions
ConditionsYield
In benzene Disproportionation; UV-irradiation;A n/a
B 90%
O-(tert-butyl) S-(pyridin-2-yl)carbonothioate
105678-24-8

O-(tert-butyl) S-(pyridin-2-yl)carbonothioate

L-phenylalanine, dicyclohexylammonium salt

L-phenylalanine, dicyclohexylammonium salt

A

2-Mercaptopyridine
2637-34-5

2-Mercaptopyridine

B

N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

Conditions
ConditionsYield
With triethylamine In water; N,N-dimethyl-formamide for 16h; Ambient temperature;A n/a
B 89%
N-[(1,1-dimethylethoxy)carbonyl]-L-phenylalanine 1,1-dimethylethyl ester
116400-16-9

N-[(1,1-dimethylethoxy)carbonyl]-L-phenylalanine 1,1-dimethylethyl ester

N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

Conditions
ConditionsYield
With water; iodine In acetonitrile for 5h; Heating;89%
With KSF clay In acetonitrile for 4.5h; Heating;87%
With cerium(III) chloride; sodium iodide In acetonitrile for 6h; Heating;78%
With trifluoroacetic acid
N-Boc-L-phenylalanine (1-nosyl-5-nitroindol-3-yl)methyl ester

N-Boc-L-phenylalanine (1-nosyl-5-nitroindol-3-yl)methyl ester

N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

Conditions
ConditionsYield
Stage #1: N-Boc-L-phenylalanine (1-nosyl-5-nitroindol-3-yl)methyl ester With 2-(N,N-dimethylamino)ethylthiol hydrochloride; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃; for 0.25h; Inert atmosphere;
Stage #2: With hydrogenchloride In diethyl ether; water; acetonitrile Inert atmosphere;
88%
L-phenylalanine
63-91-2

L-phenylalanine

dimethylsulfonium methylsulfate

dimethylsulfonium methylsulfate

N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

Conditions
ConditionsYield
With triethylamine In water Ambient temperature;84%
L-phenylalanine
63-91-2

L-phenylalanine

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile
58632-95-4

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile

A

2-(hydroxyimino)-2-phenylacetonitrile
825-52-5

2-(hydroxyimino)-2-phenylacetonitrile

B

N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

Conditions
ConditionsYield
With triethylamine In 1,4-dioxane; water for 3h;A n/a
B 83%
L-phenylalanine
63-91-2

L-phenylalanine

1,2,2,2-Tetrachloroethyl tert-Butyl Carbonate
98015-52-2

1,2,2,2-Tetrachloroethyl tert-Butyl Carbonate

N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

Conditions
ConditionsYield
With triethylamine In 1,4-dioxane; water at 20℃; for 6h;79%
With triethylamine In 1,4-dioxane; water at 20℃; for 5h;79%
(S)-2-tert-Butoxycarbonylamino-3-phenyl-propionic acid 2-trimethylsilanyl-ethoxymethyl ester

(S)-2-tert-Butoxycarbonylamino-3-phenyl-propionic acid 2-trimethylsilanyl-ethoxymethyl ester

N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

Conditions
ConditionsYield
With magnesium bromide In dichloromethane for 2.5h; Ambient temperature; addition at -20 deg C, 0.5 h;78%
L-phenylalanine
63-91-2

L-phenylalanine

1-(t-butoxycarbonyl)-1,2,4-triazolo<4,3-a>pyridinium-3-olate
50739-44-1

1-(t-butoxycarbonyl)-1,2,4-triazolo<4,3-a>pyridinium-3-olate

N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

Conditions
ConditionsYield
With pyridine; sodium hydroxide In 1,4-dioxane for 4h; Ambient temperature;77%
Boc-Phe-O-(F)TMSE
1174669-41-0

Boc-Phe-O-(F)TMSE

N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

Conditions
ConditionsYield
With (F)TBAF In tetrahydrofuran; N,N-dimethyl-formamide at 40℃; for 1h; Inert atmosphere; Microwave irradiation;72%
Boc-Phe-NHNHPh
17790-88-4

Boc-Phe-NHNHPh

N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

Conditions
ConditionsYield
With oxygen for 6h; tyrosinase, phosphate buffer pH 7;65%
With phosphate buffer; oxygen; tyrosinase In water; acetonitrile at 20℃; for 6h; pH=7.0;65%
L-phenylalanine
63-91-2

L-phenylalanine

N-tert-Butoxycarbonyl-N-trifluoromethylsulfonyl-4-trifluoromethylanilide
250296-58-3

N-tert-Butoxycarbonyl-N-trifluoromethylsulfonyl-4-trifluoromethylanilide

N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

Conditions
ConditionsYield
With water; triethylamine In 1,4-dioxane at 20℃; for 24h; Acylation;59%
methyl (2S)-2-amino-3-phenylpropanoate
2577-90-4

methyl (2S)-2-amino-3-phenylpropanoate

N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

(S)-methyl 2-((S)-2-(tert-butoxycarbonylamino)-3-phenylpropanamido)-3-phenylpropanoate
13122-89-9

(S)-methyl 2-((S)-2-(tert-butoxycarbonylamino)-3-phenylpropanamido)-3-phenylpropanoate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In various solvent(s) at 65℃; for 3h;100%
With 6-chloro-3-((dimethylamino)(dimethyliminio)methyl)-1H-benzo[d][1,2,3]triazol-3-ium-1-olatehexafluorophosphate(V); N-ethyl-N,N-diisopropylamine In dichloromethane98%
With 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride In Dichlorodifluoromethane; water at 20℃; for 3h;96%
N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

methyl iodide
74-88-4

methyl iodide

Boc-N-Me-Phe-OH
37553-65-4

Boc-N-Me-Phe-OH

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide100%
With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium hydride In tetrahydrofuran at 0 - 20℃; for 18.5h;100%
With sodium hydride In tetrahydrofuran at 20℃; for 18h;100%
N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

N,O-dimethylhydroxylamine*hydrochloride
6638-79-5

N,O-dimethylhydroxylamine*hydrochloride

Boc-Phe-OH N,O-dimethyl hydroxamate
87694-53-9

Boc-Phe-OH N,O-dimethyl hydroxamate

Conditions
ConditionsYield
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine In acetonitrile Acylation;100%
Stage #1: N-tert-butoxycarbonyl-L-phenylalanine With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; for 0.25h; Inert atmosphere;
Stage #2: N,O-dimethylhydroxylamine*hydrochloride With 4-methyl-morpholine In dichloromethane at 0 - 25℃; for 14h; Inert atmosphere;
100%
Stage #1: N-tert-butoxycarbonyl-L-phenylalanine With 4-methyl-morpholine; isobutyl chloroformate In dichloromethane at 0℃; for 0.333333h;
Stage #2: N,O-dimethylhydroxylamine*hydrochloride With triethylamine In dichloromethane for 1.25h;
100%
N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

L-isoleucine tert-butyl ester hydrochloride
69320-89-4

L-isoleucine tert-butyl ester hydrochloride

Boc-Phe-Ile-OtBu

Boc-Phe-Ile-OtBu

Conditions
ConditionsYield
With 4-methyl-morpholine; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate In N,N-dimethyl-formamide for 2h;100%
N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

(S)-2-(tert-butoxycarbonylamino)-N-((1S,2R)-2-hydroxy-1-indanyl)-3-phenylpropanamide
140468-58-2

(S)-2-(tert-butoxycarbonylamino)-N-((1S,2R)-2-hydroxy-1-indanyl)-3-phenylpropanamide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 1h;100%
With 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide for 18h; Ambient temperature;5.50 g
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine In N,N-dimethyl-formamide for 18h; Ambient temperature;
N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

(S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropionamide
88463-18-7

(S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropionamide

Conditions
ConditionsYield
Stage #1: N-tert-butoxycarbonyl-L-phenylalanine With chloroformic acid ethyl ester; triethylamine In tetrahydrofuran at 0℃; for 0.5h;
Stage #2: With ammonium chloride In tetrahydrofuran; water at 0℃; for 0.5h;
100%
Stage #1: N-tert-butoxycarbonyl-L-phenylalanine With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at -20℃; Inert atmosphere;
Stage #2: With ammonium hydroxide In tetrahydrofuran at -20 - 20℃;
98%
With ammonium bicarbonate; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline In chloroform Ambient temperature;91%
N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

(S)-N-tert-butoxycarbonyl-2-amino-3-phenylpropanol
66605-57-0

(S)-N-tert-butoxycarbonyl-2-amino-3-phenylpropanol

Conditions
ConditionsYield
Stage #1: N-tert-butoxycarbonyl-L-phenylalanine With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at -15℃; for 0.25h;
Stage #2: With sodium tetrahydroborate In tetrahydrofuran; water at -15℃; for 1h;
100%
With sodium tetrahydroborate; 2-(6-nitro-1-oxy-benzotriazol-3-yl)-1,1,3,3-Me4-uronium*PF6; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 0.5h;93%
Stage #1: N-tert-butoxycarbonyl-L-phenylalanine With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.5h;
Stage #2: With sodium tetrahydroborate; water In tetrahydrofuran at 0℃; for 0.5h;
92%
N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

C20H33NO4Si
130529-77-0

C20H33NO4Si

Conditions
ConditionsYield
With triethylamine In ethyl acetate at 0℃; for 30h;100%
N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

chloroacetonitrile
107-14-2

chloroacetonitrile

(S)-cyanomethyl 2-((tert-butoxycarbonyl)amino)-3-phenylpropanoate
127357-85-1

(S)-cyanomethyl 2-((tert-butoxycarbonyl)amino)-3-phenylpropanoate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃;100%
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃;100%
With triethylamine for 2h; Ambient temperature;89%
N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

1-amino-2-propene
107-11-9

1-amino-2-propene

(S)-tert-butyl (1-(allylamino)-1-oxo-3-phenylpropan-2-yl)carbamate
120125-16-8

(S)-tert-butyl (1-(allylamino)-1-oxo-3-phenylpropan-2-yl)carbamate

Conditions
ConditionsYield
With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at -25 - 20℃; for 2h;100%
With triethylamine; isobutyl chloroformate In dichloromethane at 20℃; for 15h;84%
With 4-methyl-morpholine; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide at 5℃;
With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran
N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

dibenzyl dicarbonate
31139-36-3

dibenzyl dicarbonate

N-(tert-butoxycarbonyl)-L-phenylalanine benzyl ester
66617-58-1

N-(tert-butoxycarbonyl)-L-phenylalanine benzyl ester

Conditions
ConditionsYield
With dmap In tetrahydrofuran for 0.333333h;100%
N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

3-aminodihydrothiophen-2(3H)-one hydrochloride
6038-19-3

3-aminodihydrothiophen-2(3H)-one hydrochloride

[(S)-1-(2-Oxo-tetrahydro-thiophen-3-ylcarbamoyl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester
192310-93-3

[(S)-1-(2-Oxo-tetrahydro-thiophen-3-ylcarbamoyl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane for 4h; Ambient temperature;100%
N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

(S)-tert-butyl (1-hydrazinyl-1-oxo-3-phenylpropan-2-yl)carbamate
30189-48-1

(S)-tert-butyl (1-hydrazinyl-1-oxo-3-phenylpropan-2-yl)carbamate

Conditions
ConditionsYield
With pyridine; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; hydrazine at 20℃; for 16h; Reagent/catalyst; Inert atmosphere;100%
With hydrazine hydrate In methanol for 18h;68%
(i) ClCO2Et, Et3N, THF, (ii) N2H4*H2O; Multistep reaction;
N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

benzyl bromide
100-39-0

benzyl bromide

N-(tert-butoxycarbonyl)-L-phenylalanine benzyl ester
66617-58-1

N-(tert-butoxycarbonyl)-L-phenylalanine benzyl ester

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 0 - 20℃; for 24h; Further stages;100%
With potassium carbonate In acetone Heating / reflux;99%
With potassium carbonate In acetonitrile for 24h; Reflux;93%
cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

(S)-[1-benzyl-2-(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester
109579-08-0

(S)-[1-benzyl-2-(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 16h;100%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 12h; Inert atmosphere;95%
Stage #1: cycl-isopropylidene malonate; N-tert-butoxycarbonyl-L-phenylalanine With dmap In dichloromethane for 0.166667h; Cooling with ice;
Stage #2: With dicyclohexyl-carbodiimide In dichloromethane for 10h; Cooling with ice;
77%
N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride
3945-69-5

4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride

2-tert-butoxycarbonylamino-3-phenyl-propionic acid 4,6-dimethoxy-[1,3,5]triazin-2-yl ester
1025839-59-1

2-tert-butoxycarbonylamino-3-phenyl-propionic acid 4,6-dimethoxy-[1,3,5]triazin-2-yl ester

Conditions
ConditionsYield
In 1,2-dimethoxyethane at 0℃; for 3h; Condensation;100%
1-phenylmethylpiperazine
2759-28-6

1-phenylmethylpiperazine

N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

(S)-[1-benzyl-2-(4-benzyl-piperazin-1-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester
154812-31-4

(S)-[1-benzyl-2-(4-benzyl-piperazin-1-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester

Conditions
ConditionsYield
Stage #1: N-tert-butoxycarbonyl-L-phenylalanine With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate In dichloromethane at 20℃; for 1h; Inert atmosphere;
Stage #2: 1-phenylmethylpiperazine In dichloromethane at 20℃;
100%
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 8h;91%
With diethyl cyanophosphonate; triethylamine In dichloromethane Condensation;
N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

(3RS)-3-amino-1-cyclohexyl-carbonylmethyl-2,3-dihydro-5-ethyl-9-methyl-1H-1,4-benzodiazepin-2-one
205996-41-4

(3RS)-3-amino-1-cyclohexyl-carbonylmethyl-2,3-dihydro-5-ethyl-9-methyl-1H-1,4-benzodiazepin-2-one

(3RS)-1-cyclohexylcarbonylmethyl-3-[N-tert-butoxycarbonyl-(S)-phenylalanyl]amino-5-ethyl-2,3-dihydro-9-methyl-1H-1,4-benzodiazepin-2-one
205998-78-3

(3RS)-1-cyclohexylcarbonylmethyl-3-[N-tert-butoxycarbonyl-(S)-phenylalanyl]amino-5-ethyl-2,3-dihydro-9-methyl-1H-1,4-benzodiazepin-2-one

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; Acylation;100%
cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

(2'S)-5-<(1-hydroxy-3-phenyl-2-t-butoxycarbonylamino)-propylidene>-2,2-dimethyl-1,3-dioxane-4,6-dione
112700-36-4, 112700-37-5

(2'S)-5-<(1-hydroxy-3-phenyl-2-t-butoxycarbonylamino)-propylidene>-2,2-dimethyl-1,3-dioxane-4,6-dione

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃;100%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃;
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 25℃; for 14h; Inert atmosphere;
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃;
methanol
67-56-1

methanol

N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

(S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester
51987-73-6

(S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester

Conditions
ConditionsYield
With thionyl chloride at 0 - 20℃; for 24h;100%
With 4-methyl-morpholine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride In water for 3h;96%
With cyano-hydroxyimino-acetic acid 2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester; sodium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In water; acetonitrile95%
N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

cycloleucine methyl ester
78388-61-1

cycloleucine methyl ester

BocPhe-cLeuOMe

BocPhe-cLeuOMe

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In various solvent(s) at 65℃; for 3h;100%
N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

o-SSEt-phenol
714229-46-6

o-SSEt-phenol

2-tert-butoxycarbonylamino-3-phenyl-propionic acid 2-ethyldisulfanyl-phenyl ester
714229-47-7

2-tert-butoxycarbonylamino-3-phenyl-propionic acid 2-ethyldisulfanyl-phenyl ester

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran; dichloromethane at 20℃; for 18h;100%
N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

allyl bromide
106-95-6

allyl bromide

2-tert-butoxycarbonylamino-3-phenylpropionic acid allyl ester
160788-63-6

2-tert-butoxycarbonylamino-3-phenylpropionic acid allyl ester

Conditions
ConditionsYield
With potassium hydrogencarbonate In N,N-dimethyl-formamide at 0 - 20℃; for 15h;100%
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 22℃; for 16h; Inert atmosphere;99%
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 20℃;98%
With potassium hydrogencarbonate In N,N-dimethyl-formamide at 0 - 20℃; for 15h; Inert atmosphere;92%
With tetrabutylammomium bromide; potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere;
N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

4,6-O-di(tert-butyl)silanediyl-D-glucal
191593-14-3

4,6-O-di(tert-butyl)silanediyl-D-glucal

3-O-(N-tert-butoxycarbonyl-L-phenylalanyl)-4,6-O-di-tert-butylsilanediyl-D-glucal

3-O-(N-tert-butoxycarbonyl-L-phenylalanyl)-4,6-O-di-tert-butylsilanediyl-D-glucal

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane100%
N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

Propargylamine
2450-71-7

Propargylamine

(S)-tert-butyl (1-oxo-3-phenyl-1-(prop-2-yn-1-ylamino)propan-2-yl)carbamate
461638-99-3

(S)-tert-butyl (1-oxo-3-phenyl-1-(prop-2-yn-1-ylamino)propan-2-yl)carbamate

Conditions
ConditionsYield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In dichloromethane for 2h; Inert atmosphere; Reflux;100%
With benzotriazol-1-ol; diisopropyl-carbodiimide In dichloromethane at 0 - 20℃; for 16h; Inert atmosphere;95%
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 12h; Inert atmosphere;93%
5-{4-[2-amino-2-(1H-benzoimidazol-2-yl)-ethyl]-phenyl}-2-tert-butyl-1,1-dioxo-1λ6-isothiazolidin-3-one; compound with trifluoro-acetic acid

5-{4-[2-amino-2-(1H-benzoimidazol-2-yl)-ethyl]-phenyl}-2-tert-butyl-1,1-dioxo-1λ6-isothiazolidin-3-one; compound with trifluoro-acetic acid

N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

tert-butyl (1S)-2-[((1S)-1-(1H-benzimidazol-2-yl)-2-4-[(5S)-2-tert-butyl-1,1-dioxido-3-oxoisothiazolidin-5-yl]phenylethyl)amino]-1-benzyl-2-oxoethylcarbamate
918959-20-3

tert-butyl (1S)-2-[((1S)-1-(1H-benzimidazol-2-yl)-2-4-[(5S)-2-tert-butyl-1,1-dioxido-3-oxoisothiazolidin-5-yl]phenylethyl)amino]-1-benzyl-2-oxoethylcarbamate

Conditions
ConditionsYield
Stage #1: N-tert-butoxycarbonyl-L-phenylalanine With N-ethyl-N,N-diisopropylamine; HATU In 1-methyl-pyrrolidin-2-one for 0.0833333h;
Stage #2: 5-{4-[2-amino-2-(1H-benzoimidazol-2-yl)-ethyl]-phenyl}-2-tert-butyl-1,1-dioxo-1λ6-isothiazolidin-3-one; compound with trifluoro-acetic acid With N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one; dimethyl sulfoxide at 20℃;
100%
N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

Benzhydrylamine
91-00-9

Benzhydrylamine

N-α-t-butoxycarbonyl-L-phenylalanine-N-benzhydrylamide
143553-18-8

N-α-t-butoxycarbonyl-L-phenylalanine-N-benzhydrylamide

Conditions
ConditionsYield
With diethyl cyanophosphonate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0 - 20℃; for 16h;100%

13734-34-4Relevant articles and documents

Synthesis of cyclic peptides through ring-closing metathesis of photolabile protecting groups

Hoffmann, Judith,Kazmaier, Uli

, p. 411 - 420 (2015)

The new photolabile protecting groups 4-allyl-5-methoxy-3-nitrobenzyl (AMNB) and 4-allyl-5-methoxy-3-nitrobenzyloxycarbonyl (AMNBOC) with an allylic side chain can easily be obtained from vanillin. These protecting groups can be introduced on the C- as well as on the N-terminus of peptides, and subsequent ring-closing metatheses provides a straightforward protocol for the synthesis of cyclic peptides. The protecting groups can be removed under UVA irradiation (365 nm).

Reusable resin plug-bound palladium catalysts for organic synthesis

Atrash, Butrus,Reader, John,Bradley, Mark

, p. 4779 - 4782 (2003)

Resin plugs, a unique and conveniently handled form of resin, prepared by sintering high-density polyethylene (HDPE) with pre-functionalised resins, were derivatised and loaded with palladium(0). These 'plugs' were used in the preparation of a Suzuki reaction based library and the removal of allyl ester protecting groups. The 'plugs of catalyst' were easily separated from the reaction mixture and were re-used multiple times with minimal loss of activity.

β-Sheet to Helical-Sheet Evolution Induced by Topochemical Polymerization: Cross-α-Amyloid-like Packing in a Pseudoprotein with Gly-Phe-Gly Repeats

Hema, Kuntrapakam,Sureshan, Kana M.

, p. 8854 - 8859 (2020)

Protein-mimics are of great interest for their structure, stability, and properties. We are interested in the synthesis of protein-mimics containing triazole linkages as peptide-bond surrogate by topochemical azide-alkyne cycloaddition (TAAC) polymerization of azide- and alkyne-modified peptides. The rationally designed dipeptide N3-CH2CO-Phe-NHCH2CCH (1) crystallized in a parallel β-sheet arrangement and are head-to-tail aligned in a direction perpendicular to the β-sheet-direction. Upon heating, crystals of 1 underwent single-crystal-to-single-crystal polymerization forming a triazole-linked pseudoprotein with Gly-Phe-Gly repeats. During TAAC polymerization, the pseudoprotein evolved as helical chains. These helical chains are laterally assembled by backbone hydrogen bonding in a direction perpendicular to the helical axis to form helical sheets. This interesting helical-sheet orientation in the crystal resembles the cross-α-amyloids, where α-helices are arranged laterally as sheets.

Chiral secondary phosphine oxide pre-ligand and application thereof

-

Paragraph 0040-0043, (2021/10/20)

The invention discloses a chiral secondary phosphine oxide pre-ligand and application thereof. The structure of the ligand is as shown in Formula I, where R. 1 . R2 , R3 And R4 Hydrogen, benzyl, substituted alkyl, substituted or unsubstituted aryl. The more preferred structural formula comprises 4 structural general formulas shown in the general formula I in the following formula: I-d, and the formula is shown in the general formula. Based on the designed asymmetric catalytic reaction system, the stability and the easy preparation of the comprehensive test ligand under the hydrocarbon activation condition are synthesized, and finally the chiral secondary oxidation phosphorus precursor with the double functional groups in the oxidation and heating environment is selected. The catalyst formed by the front ligand and the active metal compound has high activity and high selectivity in the reaction of constructing a chiral center, and has the stability.

CONJUGATE OF FLUORESCENT DYE FOR THE VISUALIZATION OF PSMA EXPRESSING CELLS

-

Page/Page column 10; 15, (2021/01/23)

The invention relates to the field of organic and medicinal chemistry, as well as molecular biology, and concerns a new class of compounds for imaging PSMA expressing cells and tissues, such as prostate cancer cells. New diagnostic conjugates for the visu

Synthesis and Biological Evaluation of PSMA Ligands with Aromatic Residues and Fluorescent Conjugates Based on Them

Machulkin, Aleksei E.,Shafikov, Radik R.,Uspenskaya, Anastasia A.,Petrov, Stanislav A.,Ber, Anton P.,Skvortsov, Dmitry A.,Nimenko, Ekaterina A.,Zyk, Nikolay U.,Smirnova, Galina B.,Pokrovsky, Vadim S.,Abakumov, Maxim A.,Saltykova, Irina V.,Akhmirov, Rauf T.,Garanina, Anastasiia S.,Polshakov, Vladimir I.,Saveliev, Oleg Y.,Ivanenkov, Yan A.,Aladinskaya, Anastasiya V.,Finko, Alexander V.,Yamansarov, Emil U.,Krasnovskaya, Olga O.,Erofeev, Alexander S.,Gorelkin, Petr V.,Dontsova, Olga A.,Beloglazkina, Elena K.,Zyk, Nikolay V.,Khazanova, Elena S.,Majouga, Alexander G.

supporting information, p. 4532 - 4552 (2021/05/06)

Prostate-specific membrane antigen (PSMA), also known as glutamate carboxypeptidase II (GCPII), is a suitable target for specific delivery of antitumor drugs and diagnostic agents due to its overexpression in prostate cancer cells. In the current work, we describe the design, synthesis, and biological evaluation of novel low-molecular PSMA ligands and conjugates with fluorescent dyes FAM-5, SulfoCy5, and SulfoCy7. In vitro evaluation of synthesized PSMA ligands on the activity of PSMA shows that the addition of aromatic amino acids into a linker structure leads to a significant increase in inhibition. The conjugates of the most potent ligand with FAM-5 as well as SulfoCy5 demonstrated high affinities to PSMA-expressing tumor cells in vitro. In vivo biodistribution in 22Rv1 xenografts in Balb/c nude mice of PSMA-SulfoCy5 and PSMA-SulfoCy7 conjugates with a novel PSMA ligand demonstrated good visualization of PSMA-expressing tumors. Also, the conjugate PSMA-SulfoCy7 demonstrated the absence of any explicit toxicity up to 87.9 mg/kg.

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