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29022-11-5

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29022-11-5 Usage

Chemical Properties

white to light yellow crystal powde

Uses

N-Fmoc-glycine is an N-Fmoc-protected form of Glycine (G615990). Glycine is a nonessential amino acid that acts as an inhibitory neyrotransmitter in the vertebrate central nervous system. Glycine also posesses cytoprotective against oxidant damage in the kidney.

General Description

The product number for this product was previously 04-12-1001.To obtain a certificate of analysis (CoA) of a lot that begins with the letter “A”, please select the option in the right hand menu “Request a COA for Lot#s starting with A”.

Check Digit Verification of cas no

The CAS Registry Mumber 29022-11-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,9,0,2 and 2 respectively; the second part has 2 digits, 1 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 29022-11:
(7*2)+(6*9)+(5*0)+(4*2)+(3*2)+(2*1)+(1*1)=85
85 % 10 = 5
So 29022-11-5 is a valid CAS Registry Number.
InChI:InChI=1/C17H15NO4/c19-16(20)9-18-17(21)22-10-15-13-7-3-1-5-11(13)12-6-2-4-8-14(12)15/h1-8,15H,9-10H2,(H,18,21)(H,19,20)/p-1

29022-11-5 Well-known Company Product Price

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  • TCI America

  • (F0293)  N-[(9H-Fluoren-9-ylmethoxy)carbonyl]glycine  >98.0%(HPLC)(T)

  • 29022-11-5

  • 5g

  • 205.00CNY

  • Detail
  • TCI America

  • (F0293)  N-[(9H-Fluoren-9-ylmethoxy)carbonyl]glycine  >98.0%(HPLC)(T)

  • 29022-11-5

  • 25g

  • 595.00CNY

  • Detail
  • Alfa Aesar

  • (B21050)  N-Fmoc-glycine, 98%   

  • 29022-11-5

  • 1g

  • 296.0CNY

  • Detail
  • Alfa Aesar

  • (B21050)  N-Fmoc-glycine, 98%   

  • 29022-11-5

  • 5g

  • 1105.0CNY

  • Detail
  • Aldrich

  • (47627)  Fmoc-Gly-OH  ≥98.0% (T)

  • 29022-11-5

  • 47627-5G-F

  • 269.10CNY

  • Detail
  • Aldrich

  • (47627)  Fmoc-Gly-OH  ≥98.0% (T)

  • 29022-11-5

  • 47627-50G-F

  • 741.78CNY

  • Detail
  • Aldrich

  • (47627)  Fmoc-Gly-OH  ≥98.0% (T)

  • 29022-11-5

  • 47627-250G-F

  • 2,130.57CNY

  • Detail

29022-11-5SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name FMOC-Glycine

1.2 Other means of identification

Product number -
Other names N-Fmoc-glycine

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:29022-11-5 SDS

29022-11-5Synthetic route

4-((tert-butyldimethylsilyl)oxy)benzyl (((9H-fluoren-9-yl)methoxy)carbonyl)glycinate

4-((tert-butyldimethylsilyl)oxy)benzyl (((9H-fluoren-9-yl)methoxy)carbonyl)glycinate

N-(fluoren-9-ylmethoxycarbonyl)glycine
29022-11-5

N-(fluoren-9-ylmethoxycarbonyl)glycine

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane at 20℃; for 0.0833333h; Reagent/catalyst;97%
glycine
56-40-6

glycine

polymer-bound Fmoc-O-succinimide

polymer-bound Fmoc-O-succinimide

N-(fluoren-9-ylmethoxycarbonyl)glycine
29022-11-5

N-(fluoren-9-ylmethoxycarbonyl)glycine

Conditions
ConditionsYield
With potassium carbonate In acetone at 20℃; for 24h;96%
9-fluorenylmethyl 4,6-dimethoxy-1,3,5-triazinyl carbonate
909114-66-5

9-fluorenylmethyl 4,6-dimethoxy-1,3,5-triazinyl carbonate

glycine
56-40-6

glycine

N-(fluoren-9-ylmethoxycarbonyl)glycine
29022-11-5

N-(fluoren-9-ylmethoxycarbonyl)glycine

Conditions
ConditionsYield
With sodium carbonate In acetonitrile at 20℃; for 0.333333h;96%
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
82911-69-1

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

glycine
56-40-6

glycine

N-(fluoren-9-ylmethoxycarbonyl)glycine
29022-11-5

N-(fluoren-9-ylmethoxycarbonyl)glycine

Conditions
ConditionsYield
With sodium hydrogencarbonate In acetone Ambient temperature;95%
Stage #1: glycine With N-cyclohexyl-cyclohexanamine In acetone at 20℃;
Stage #2: N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide With sodium carbonate In water; acetonitrile at 0 - 20℃; pH=8;
Stage #3: With potassium hydrogensulfate In water; acetonitrile pH=2 - 3;
86%
With pyridine In methanol
With sodium carbonate In 1,4-dioxane; water at 20℃; for 18h;
glycine
56-40-6

glycine

4-(9-fluorenylmethoxycarbonyloxy) phenyl dimethylsulfonium methylsulfate

4-(9-fluorenylmethoxycarbonyloxy) phenyl dimethylsulfonium methylsulfate

N-(fluoren-9-ylmethoxycarbonyl)glycine
29022-11-5

N-(fluoren-9-ylmethoxycarbonyl)glycine

Conditions
ConditionsYield
With triethylamine In water Ambient temperature;94%
1-[(9-fluorenylmethyloxycarbonyl)]benzotriazole
1131148-55-4

1-[(9-fluorenylmethyloxycarbonyl)]benzotriazole

glycine
56-40-6

glycine

N-(fluoren-9-ylmethoxycarbonyl)glycine
29022-11-5

N-(fluoren-9-ylmethoxycarbonyl)glycine

Conditions
ConditionsYield
With triethylamine In water; acetonitrile at 20℃; for 2h;94%
N-(((9H-fluoren-9-yl)methoxy)carbonyloxy)-2-morpholino-2-oxoacetimidoyl cyanide
1370440-40-6

N-(((9H-fluoren-9-yl)methoxy)carbonyloxy)-2-morpholino-2-oxoacetimidoyl cyanide

glycine
56-40-6

glycine

N-(fluoren-9-ylmethoxycarbonyl)glycine
29022-11-5

N-(fluoren-9-ylmethoxycarbonyl)glycine

Conditions
ConditionsYield
With sodium hydrogencarbonate In water; acetone93.5%
N-(((9H-fluoren-9-yl)methoxy)carbonyloxy)-2-amino-2-oxoacetimidoyl cyanide
1370440-28-0

N-(((9H-fluoren-9-yl)methoxy)carbonyloxy)-2-amino-2-oxoacetimidoyl cyanide

glycine
56-40-6

glycine

N-(fluoren-9-ylmethoxycarbonyl)glycine
29022-11-5

N-(fluoren-9-ylmethoxycarbonyl)glycine

Conditions
ConditionsYield
With sodium carbonate In water; acetone at 20℃; for 4h; pH=9 - 10;93%
With sodium hydrogencarbonate In water; acetone90.8%
(9H-fluoren-9-yl)methyl 2-oxopyridin-1(2H)-yl carbonate
1235983-29-5

(9H-fluoren-9-yl)methyl 2-oxopyridin-1(2H)-yl carbonate

glycine
56-40-6

glycine

N-(fluoren-9-ylmethoxycarbonyl)glycine
29022-11-5

N-(fluoren-9-ylmethoxycarbonyl)glycine

Conditions
ConditionsYield
With sodium hydrogencarbonate In water; acetone92.8%
diethyl 2-{[(9H-fluoren-9-yl)methoxy]carbonyloxyimino}-2-cyanoacetate
1235983-26-2

diethyl 2-{[(9H-fluoren-9-yl)methoxy]carbonyloxyimino}-2-cyanoacetate

glycine
56-40-6

glycine

N-(fluoren-9-ylmethoxycarbonyl)glycine
29022-11-5

N-(fluoren-9-ylmethoxycarbonyl)glycine

Conditions
ConditionsYield
With sodium hydrogencarbonate In water; acetone92.1%
N-(((9H-fluoren-9-yl)methoxy)carbonyloxy)-2-oxo-2-(piperidin-1-yl)acetimidoyl cyanide
1370440-36-0

N-(((9H-fluoren-9-yl)methoxy)carbonyloxy)-2-oxo-2-(piperidin-1-yl)acetimidoyl cyanide

glycine
56-40-6

glycine

N-(fluoren-9-ylmethoxycarbonyl)glycine
29022-11-5

N-(fluoren-9-ylmethoxycarbonyl)glycine

Conditions
ConditionsYield
With sodium hydrogencarbonate In water; acetone92.1%
N-(((9H-fluoren-9-yl)methoxy)carbonyloxy)-2-(ethylamino)-2-oxoacetimidoyl cyanide
1370440-32-6

N-(((9H-fluoren-9-yl)methoxy)carbonyloxy)-2-(ethylamino)-2-oxoacetimidoyl cyanide

glycine
56-40-6

glycine

N-(fluoren-9-ylmethoxycarbonyl)glycine
29022-11-5

N-(fluoren-9-ylmethoxycarbonyl)glycine

Conditions
ConditionsYield
With sodium hydrogencarbonate In water; acetone91.8%
N-{[(9H-fluoren-9-yl)methoxy]carbonyloxy}picolinimidoyl cyanide
1235983-28-4

N-{[(9H-fluoren-9-yl)methoxy]carbonyloxy}picolinimidoyl cyanide

glycine
56-40-6

glycine

N-(fluoren-9-ylmethoxycarbonyl)glycine
29022-11-5

N-(fluoren-9-ylmethoxycarbonyl)glycine

Conditions
ConditionsYield
With sodium hydrogencarbonate In water; acetone91.6%
Fmoc-Gly-N3
329308-95-4

Fmoc-Gly-N3

N-(fluoren-9-ylmethoxycarbonyl)glycine
29022-11-5

N-(fluoren-9-ylmethoxycarbonyl)glycine

Conditions
ConditionsYield
With sodium tetrahydroborate In tetrahydrofuran; water cooling;90%
3-(9-Fluorenylmethoxycarbonyl)-benzothiazoline-2-thione
100803-86-9

3-(9-Fluorenylmethoxycarbonyl)-benzothiazoline-2-thione

glycine
56-40-6

glycine

N-(fluoren-9-ylmethoxycarbonyl)glycine
29022-11-5

N-(fluoren-9-ylmethoxycarbonyl)glycine

Conditions
ConditionsYield
With sodium hydroxide In 1,4-dioxane for 12h; Ambient temperature;88%
glycine
56-40-6

glycine

Carbonic acid 1,3-dioxo-1,3-dihydro-isoindol-2-yl ester 9H-fluoren-9-ylmethyl ester

Carbonic acid 1,3-dioxo-1,3-dihydro-isoindol-2-yl ester 9H-fluoren-9-ylmethyl ester

N-(fluoren-9-ylmethoxycarbonyl)glycine
29022-11-5

N-(fluoren-9-ylmethoxycarbonyl)glycine

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 20℃; for 2h;88%
(fluorenylmethoxy)carbonyl chloride
28920-43-6

(fluorenylmethoxy)carbonyl chloride

glycine
56-40-6

glycine

N-(fluoren-9-ylmethoxycarbonyl)glycine
29022-11-5

N-(fluoren-9-ylmethoxycarbonyl)glycine

Conditions
ConditionsYield
In ethanol; water at 60℃; for 4h; chemoselective reaction;85%
Stage #1: (fluorenylmethoxy)carbonyl chloride; glycine With sodium carbonate In 1,4-dioxane; water at 0 - 20℃; for 4h;
Stage #2: With hydrogenchloride In water pH=2;
85%
With sodium carbonate; N-ethyl-N,N-diisopropylamine In water; N,N-dimethyl-formamide 1.) 0 deg C, 30 min; 2.) up to RT, 1 h;62%
(9-fluorenyl)methyl pentafluorophenyl carbonate
88744-04-1

(9-fluorenyl)methyl pentafluorophenyl carbonate

glycine
56-40-6

glycine

N-(fluoren-9-ylmethoxycarbonyl)glycine
29022-11-5

N-(fluoren-9-ylmethoxycarbonyl)glycine

Conditions
ConditionsYield
With sodium hydrogencarbonate In water; acetone Ambient temperature;84%
methyl (((9H-fluoren-9-yl)methoxy)carbonyl)glycinate
121616-32-8

methyl (((9H-fluoren-9-yl)methoxy)carbonyl)glycinate

N-(fluoren-9-ylmethoxycarbonyl)glycine
29022-11-5

N-(fluoren-9-ylmethoxycarbonyl)glycine

Conditions
ConditionsYield
With water; sodium hydroxide In isopropyl alcohol at 20℃; for 1h; chemoselective reaction;84%
diethyl 2-{[(9H-fluoren-9-yl)methoxy]carbonyloxyimino}malonate
1235983-25-1

diethyl 2-{[(9H-fluoren-9-yl)methoxy]carbonyloxyimino}malonate

glycine
56-40-6

glycine

N-(fluoren-9-ylmethoxycarbonyl)glycine
29022-11-5

N-(fluoren-9-ylmethoxycarbonyl)glycine

Conditions
ConditionsYield
With sodium hydrogencarbonate In water; acetone82.9%
Carbonic acid 3,5-dioxo-4-aza-tricyclo[5.2.1.02,6]dec-8-en-4-yl ester 9H-fluoren-9-ylmethyl ester
99503-04-5

Carbonic acid 3,5-dioxo-4-aza-tricyclo[5.2.1.02,6]dec-8-en-4-yl ester 9H-fluoren-9-ylmethyl ester

glycine
56-40-6

glycine

N-(fluoren-9-ylmethoxycarbonyl)glycine
29022-11-5

N-(fluoren-9-ylmethoxycarbonyl)glycine

Conditions
ConditionsYield
With tertiary amine In 1,4-dioxane; water for 3h;81%
N-Fmoc-glycine 2-(2-acetylphenyl)-1-methylethyl ester
618068-91-0

N-Fmoc-glycine 2-(2-acetylphenyl)-1-methylethyl ester

N-(fluoren-9-ylmethoxycarbonyl)glycine
29022-11-5

N-(fluoren-9-ylmethoxycarbonyl)glycine

Conditions
ConditionsYield
In acetonitrile for 4h; Photolysis;56%
{[(9H-fluoren-9-yl)methoxy]carbonyloxy}carbonimidoyl dicyanide
1235983-27-3

{[(9H-fluoren-9-yl)methoxy]carbonyloxy}carbonimidoyl dicyanide

glycine
56-40-6

glycine

N-(fluoren-9-ylmethoxycarbonyl)glycine
29022-11-5

N-(fluoren-9-ylmethoxycarbonyl)glycine

Conditions
ConditionsYield
With sodium hydrogencarbonate In water; acetone48.5%
C20H23NO4Si

C20H23NO4Si

N-(fluoren-9-ylmethoxycarbonyl)glycine
29022-11-5

N-(fluoren-9-ylmethoxycarbonyl)glycine

Conditions
ConditionsYield
With methanol In dichloromethane for 0.5h; Ambient temperature; Yield given;
PEGA1900-resin-NH-(CO(CH2)7)-OCOCH2NHFmoc

PEGA1900-resin-NH-(CO(CH2)7)-OCOCH2NHFmoc

N-(fluoren-9-ylmethoxycarbonyl)glycine
29022-11-5

N-(fluoren-9-ylmethoxycarbonyl)glycine

Conditions
ConditionsYield
With chymotrypsin In phosphate buffer for 16h; pH=8;
PEGA1900-resin-NH-(p-COCH2OC6H4CH2)-OCOCH2NHFmoc

PEGA1900-resin-NH-(p-COCH2OC6H4CH2)-OCOCH2NHFmoc

N-(fluoren-9-ylmethoxycarbonyl)glycine
29022-11-5

N-(fluoren-9-ylmethoxycarbonyl)glycine

Conditions
ConditionsYield
With chymotrypsin In phosphate buffer for 16h; pH=8;
Fmoc-Gly-MFE

Fmoc-Gly-MFE

A

N-(fluoren-9-ylmethoxycarbonyl)glycine
29022-11-5

N-(fluoren-9-ylmethoxycarbonyl)glycine

B

3-O-methylfluorescein
70672-05-8

3-O-methylfluorescein

Conditions
ConditionsYield
With ethylenediaminetetraacetic acid; DL-dithiothreitol; cathepsin B In phosphate buffer at 37℃; pH=6.7; Enzyme kinetics;
(fluorenylmethoxy)carbonyl chloride
28920-43-6

(fluorenylmethoxy)carbonyl chloride

A

N-(fluoren-9-ylmethoxycarbonyl)glycine
29022-11-5

N-(fluoren-9-ylmethoxycarbonyl)glycine

B

N-(9-fluorenylmethoxycarbonyl)-3-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-L-serine pentafluorophenyl ester

N-(9-fluorenylmethoxycarbonyl)-3-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-L-serine pentafluorophenyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 95 percent / Et3N / CH2Cl2 / 1 h / 20 °C
2: 96 percent / aq. Na2CO3 / acetonitrile / 0.33 h / 20 °C
View Scheme
N-(fluoren-9-ylmethoxycarbonyl)glycine
29022-11-5

N-(fluoren-9-ylmethoxycarbonyl)glycine

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

N,O-dimethylhydroxylamine*hydrochloride

(9H-fluoren-9-yl)methyl (2-(methoxy(methyl)amino)-2-oxoethyl)carbamate
156939-65-0

(9H-fluoren-9-yl)methyl (2-(methoxy(methyl)amino)-2-oxoethyl)carbamate

Conditions
ConditionsYield
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 4h; Inert atmosphere;100%
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;98%
Stage #1: N-(fluoren-9-ylmethoxycarbonyl)glycine With trichloroacetonitrile; triphenylphosphine In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;
Stage #2: N,O-dimethylhydroxylamine*hydrochloride With triethylamine In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;
89%
N-(fluoren-9-ylmethoxycarbonyl)glycine
29022-11-5

N-(fluoren-9-ylmethoxycarbonyl)glycine

5-Nitrosalicylaldehyde
97-51-8

5-Nitrosalicylaldehyde

Val-Ala-Gly-Phe-Wang resin

Val-Ala-Gly-Phe-Wang resin

A

(S)-2-(2-{(S)-2-[(S)-2-(2-Hydroxy-5-nitro-benzylamino)-3-methyl-butyrylamino]-propionylamino}-acetylamino)-3-phenyl-propionic acid

(S)-2-(2-{(S)-2-[(S)-2-(2-Hydroxy-5-nitro-benzylamino)-3-methyl-butyrylamino]-propionylamino}-acetylamino)-3-phenyl-propionic acid

B

(S)-2-[2-((S)-2-{(S)-2-[(2-Amino-acetyl)-(2-hydroxy-5-nitro-benzyl)-amino]-3-methyl-butyrylamino}-propionylamino)-acetylamino]-3-phenyl-propionic acid

(S)-2-[2-((S)-2-{(S)-2-[(2-Amino-acetyl)-(2-hydroxy-5-nitro-benzyl)-amino]-3-methyl-butyrylamino}-propionylamino)-acetylamino]-3-phenyl-propionic acid

Conditions
ConditionsYield
Multistep reaction;A n/a
B 100%
N-(fluoren-9-ylmethoxycarbonyl)glycine
29022-11-5

N-(fluoren-9-ylmethoxycarbonyl)glycine

Fmoc-Lys(Dde)-Rink-PS-resin

Fmoc-Lys(Dde)-Rink-PS-resin

{1-carbamoyl-5-[2-(9H-fluoren-9-ylmethoxycarbonylamino)-acetylamino]-pentyl}-carbamic acid 9H-fluoren-9-ylmethyl ester

{1-carbamoyl-5-[2-(9H-fluoren-9-ylmethoxycarbonylamino)-acetylamino]-pentyl}-carbamic acid 9H-fluoren-9-ylmethyl ester

Conditions
ConditionsYield
Stage #1: Fmoc-Lys(Dde)-Rink-PS-resin With 1H-imidazole; 1-methyl-pyrrolidin-2-one; hydroxylamine hydrochloride In dichloromethane for 3h;
Stage #2: N-(fluoren-9-ylmethoxycarbonyl)glycine With benzotriazol-1-ol; dacarbazine In N,N-dimethyl-formamide
Stage #3: With chlorotriisopropylsilane; trifluoroacetic acid In dichloromethane
100%
Pro-Val-Leu-Cys(Trt)-Ala-Wang resin

Pro-Val-Leu-Cys(Trt)-Ala-Wang resin

N-(fluoren-9-ylmethoxycarbonyl)glycine
29022-11-5

N-(fluoren-9-ylmethoxycarbonyl)glycine

Gly-Pro-Val-Leu-Cys(Trt)-Ala-Wang resin

Gly-Pro-Val-Leu-Cys(Trt)-Ala-Wang resin

Conditions
ConditionsYield
Stage #1: Pro-Val-Leu-Cys(Trt)-Ala-Wang resin; N-(fluoren-9-ylmethoxycarbonyl)glycine With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 3h;
Stage #2: With piperidine In N,N-dimethyl-formamide at 20℃; for 0.25h;
100%
N-(fluoren-9-ylmethoxycarbonyl)glycine
29022-11-5

N-(fluoren-9-ylmethoxycarbonyl)glycine

Fmoc-Gly-NH2
115057-37-9

Fmoc-Gly-NH2

Conditions
ConditionsYield
With N-hydroxybenzotriazole ammonium salt; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 20℃;100%
Stage #1: N-(fluoren-9-ylmethoxycarbonyl)glycine With Rink amide resin after treatment with piperidine in DMF; benzotriazol-1-ol; dacarbazine In N,N-dimethyl-formamide at 120℃; for 0.0833333h; microwave irradiation;
Stage #2: With trifluoroacetic acid In dichloromethane at 20℃; for 1h;
93%
Stage #1: N-(fluoren-9-ylmethoxycarbonyl)glycine With 1,3,5-trichloro-2,4,6-triazine; potassium carbonate In tetrahydrofuran for 0.0166667h; Milling;
Stage #2: With ammonium thiocyanate In tetrahydrofuran for 0.0833333h; Milling;
86%
N-(fluoren-9-ylmethoxycarbonyl)glycine
29022-11-5

N-(fluoren-9-ylmethoxycarbonyl)glycine

monomethoxy-polyethylene glycol

monomethoxy-polyethylene glycol

N-(9-fluorenylmethoxycarbonyl)glycine terminated monomethoxy-polyethylene glycol

N-(9-fluorenylmethoxycarbonyl)glycine terminated monomethoxy-polyethylene glycol

Conditions
ConditionsYield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h;100%
C16H17N
1075176-19-0

C16H17N

N-(fluoren-9-ylmethoxycarbonyl)glycine
29022-11-5

N-(fluoren-9-ylmethoxycarbonyl)glycine

C33H30N2O3
1075176-20-3

C33H30N2O3

Conditions
ConditionsYield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran100%
N-(fluoren-9-ylmethoxycarbonyl)glycine
29022-11-5

N-(fluoren-9-ylmethoxycarbonyl)glycine

N-Fmoc L-Phe
35661-40-6

N-Fmoc L-Phe

Fmoc-(tBu)Asp-OH
71989-14-5

Fmoc-(tBu)Asp-OH

Fmoc-Arg(Pbf)-OH
119831-72-0

Fmoc-Arg(Pbf)-OH

(S)-6-allyloxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-hexanoic acid
146982-27-6

(S)-6-allyloxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-hexanoic acid

H-Asp(OtBu)-Phe-Lys(Aloc)-Arg(Pmc)-Gly-OH

H-Asp(OtBu)-Phe-Lys(Aloc)-Arg(Pmc)-Gly-OH

Conditions
ConditionsYield
Stage #1: N-(fluoren-9-ylmethoxycarbonyl)glycine With N-ethyl-N,N-diisopropylamine In methanol; dichloromethane for 0.25h; solid phase reaction;
Stage #2: With piperidine In N,N-dimethyl-formamide for 0.166667h; Automated synthesizer; solid phase reaction;
Stage #3: N-Fmoc L-Phe; Fmoc-(tBu)Asp-OH; Fmoc-Arg(Pbf)-OH; (S)-6-allyloxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-hexanoic acid Further stages;
100%
C96H146N8O8S
1258442-42-0

C96H146N8O8S

N-(fluoren-9-ylmethoxycarbonyl)glycine
29022-11-5

N-(fluoren-9-ylmethoxycarbonyl)glycine

C112H157N9O11S

C112H157N9O11S

Conditions
ConditionsYield
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃;100%

29022-11-5Relevant articles and documents

Large molecular assembly of amphotericin B formed in ergosterol-containing membrane evidenced by solid-state NMR of intramolecular bridged derivative

Matsumori, Nobuaki,Sawada, Yuri,Murata, Michio

, p. 11977 - 11984 (2006)

Amphotericin B (AmB 1) is known to assemble and form an ion channel across biomembranes. We have recently reported that conformation-restricted derivatives of AmB 2-4 show different ergosterol preferences in ion-channel assays, which suggested that the orientation of the mycosamine strongly affects the sterol selectivity of AmB. The data allowed us to assume that compound 3 showing the highest selectivity would reflect the active conformation of AmB in the channel assembly. In this study, to gain further insight into the active conformation of AmB, we prepared a new intramolecular-bridged derivative 5, where the linker encompassed a hydrophilic glycine moiety. The derivative has almost equivalent ion-channel activity to those of AmB and 3. The antifungal activity of 5 compared with 3 improves significantly, possibly because the increasing hydrophilicity in the linker enhances the penetrability through the fungal cell wall. Conformation of 5 was well converged and very similar to that of 3, thus further supporting the notion that the conformations of these derivatives reproduce the active structure of AmB in the channel complex. Then we used the derivative to probe the mobility of AmB in the membrane by solid-state NMR. To measure dipolar couplings and chemical shift anisotropies, we incorporated [1-13C,15N]glycine into the linker. The results indicate that 5 is mostly immobilized in ergosterol-containing DMPC bilayers, implying formation of large aggregates of 5. Meanwhile some fraction of 5 remains mobile in sterol-free DMPC bilayers, suggesting promotion of Amb aggregation by ergosterol.

Synthesis and characterization of a photocleavable collagen-like peptide

Li, Chunqiang,Ornelas, Alfredo,Williams, Kaitlyn N.,Hatch, Kevin A.,Paez, Aurelio,Aguilar, Angela C.,Ellis, Cameron C.,Tasnim, Nishat,Ray, Supriyo,Dirk, Carl W.,Boland, Thomas,Joddar, Binata,Michael, Katja

, p. 1000 - 1013 (2018)

A 34-amino acid long collagen-like peptide rich in proline, hydroxyproline, and glycine, and with four photoreactive N-acyl-7-nitroindoline units incorporated into the peptide backbone was synthesized by on-resin fragment condensation. Its circular dichroism supports a stable triple helix structure. The built-in photochemical function enables the decomposition of the peptide into small peptide fragments by illumination with UV light of 350 nm in aqueous solution. Illumination of a thin film of the peptide, or a thin film of a photoreactive amino acid model compound containing a 5-bromo-7-nitroindoline moiety, with femtosecond laser light at 710 nm allows for the creation of well-resolved micropatterns. The cytocompatibility of the peptide was demonstrated using human mesenchymal stem cells and mouse embryonic fibroblasts. Our data show that the full-length peptide is cytocompatible as it can support cell growth and maintain cell viability. In contrast, the small peptide fragments created by photolysis are somewhat cytotoxic and therefore less cytocompatible. These data suggest that biomimetic collagen-like photoreactive peptides could potentially be used for growing cells in 2D micropatterns based on patterns generated by photolysis prior to cell growth.

Fungal Dioxygenase AsqJ Is Promiscuous and Bimodal: Substrate-Directed Formation of Quinolones versus Quinazolinones

Einsiedler, Manuel,Jamieson, Cooper S.,Maskeri, Mark A.,Houk, Kendall N.,Gulder, Tobias A. M.

supporting information, p. 8297 - 8302 (2021/03/01)

Previous studies showed that the FeII/α-ketoglutarate dependent dioxygenase AsqJ induces a skeletal rearrangement in viridicatin biosynthesis in Aspergillus nidulans, generating a quinolone scaffold from benzo[1,4]diazepine-2,5-dione substrates. We report that AsqJ catalyzes an additional, entirely different reaction, simply by a change in substituent in the benzodiazepinedione substrate. This new mechanism is established by substrate screening, application of functional probes, and computational analysis. AsqJ excises H2CO from the heterocyclic ring structure of suitable benzo[1,4]diazepine-2,5-dione substrates to generate quinazolinones. This novel AsqJ catalysis pathway is governed by a single substituent within the complex substrate. This unique substrate-directed reactivity of AsqJ enables the targeted biocatalytic generation of either quinolones or quinazolinones, two alkaloid frameworks of exceptional biomedical relevance.

Unwanted hydrolysis or α/β-peptide bond formation: How long should the rate-limiting coupling step take?

Goldschmidt G?z, Viktória,Nagy, Adrienn,Farkas, Viktor,Keszei, Ern?,Perczel, András

, p. 30720 - 30728 (2019/10/28)

Nowadays, in Solid Phase Peptide Synthesis (SPPS), being either manual, automated, continuous flow or microwave-assisted, the reaction with various coupling reagents takes place via in situ active ester formation. In this study, the formation and stability of these key active esters were investigated with time-resolved 1H NMR by using the common PyBOP/DIEA and HOBt/DIC coupling reagents for both α- and β-amino acids. Parallel to the amide bond formation, the hydrolysis of the α/β-active esters, a side reaction that is a considerable efficacy limiting factor, was studied. Based on the chemical nature/constitution of the active esters, three amino acid categories were determined: (i) the rapidly hydrolyzing ones (t 24 h) in solution. The current insight into the kinetics of this key hydrolysis side reaction serves as a guide to optimize the coupling conditions of α- and β-amino acids, thereby saving time and minimizing the amounts of reagents and amino acids to be used-all key factors of more environmentally friendly chemistry.

PHOTOREACTIVE COLLAGEN-LIKE PEPTIDES

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Paragraph 0092, (2019/04/30)

A novel 34 amino acid long collagen-like peptide rich in proline, hydroxyproline, and glycine, and with several photoreactive N-acyl-7-nitroindoline units incorporated into the peptide backbone was synthesized by on-resin fragment condensation. The circular dichroism measurement of this peptide supports a stable triple helix structure. This peptide has potential as a new biomimetic material with built-in latent photochemical functions that enable the decomposition into small peptide fragments by illumination with UV light of 350 nm. Using a photoreactive glycine derivative as a model compound for the collagen-like peptide, we demonstrate that its photolysis can also be triggered by a two-photon absorption process using a femtosecond laser at 710 nm. When a thin film of this compound is irradiated with femtosecond laser light at 710 nm the photochemistry occurs only at locations of irradiation. In addition, the collagen-like peptide is able to support mesenchymal stem cell growth, indicating its non-toxicity to these cells and its potential in tissue engineering applications.

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