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2483-46-7

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2483-46-7 Usage

Chemical Properties

Clear Oil

Uses

Nalpha, Nepsilon-Di-Boc-L-lysine is used as fine chemical intermediate, synthesis intermediates.

Check Digit Verification of cas no

The CAS Registry Mumber 2483-46-7 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,4,8 and 3 respectively; the second part has 2 digits, 4 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 2483-46:
(6*2)+(5*4)+(4*8)+(3*3)+(2*4)+(1*6)=87
87 % 10 = 7
So 2483-46-7 is a valid CAS Registry Number.
InChI:InChI=1/C16H30N2O6/c1-15(2,3)23-13(21)17-10-8-7-9-11(12(19)20)18-14(22)24-16(4,5)6/h11H,7-10H2,1-6H3,(H,17,21)(H,18,22)(H,19,20)

2483-46-7 Well-known Company Product Price

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  • Alfa Aesar

  • (H62019)  Nalpha,Nepsilon-Di-Boc-L-lysine, 98%   

  • 2483-46-7

  • 25g

  • 431.0CNY

  • Detail
  • Alfa Aesar

  • (H62019)  Nalpha,Nepsilon-Di-Boc-L-lysine, 98%   

  • 2483-46-7

  • 100g

  • 1294.0CNY

  • Detail

2483-46-7SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name (2S)-2,6-bis[(2-methylpropan-2-yl)oxycarbonylamino]hexanoic acid

1.2 Other means of identification

Product number -
Other names N2,N6-Bis[(1,1-dimethylethoxy)carbonyl]-L-lysine

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:2483-46-7 SDS

2483-46-7Synthetic route

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

L-Lysine hydrochloride
657-27-2, 10098-89-2

L-Lysine hydrochloride

Boc-Lys(Boc)-OH
2483-46-7

Boc-Lys(Boc)-OH

Conditions
ConditionsYield
With sodium hydroxide In 1,4-dioxane; water at 20℃;100%
With sodium hydroxide In 1,4-dioxane; water at 10 - 20℃; for 20h; pH=7.05 - 10;92%
Stage #1: di-tert-butyl dicarbonate; L-Lysine hydrochloride With sodium hydrogencarbonate In tetrahydrofuran; water at 0 - 20℃; for 12h;
Stage #2: di-tert-butyl dicarbonate In tetrahydrofuran; water at 0 - 20℃; for 12h;
90%
N,N'-bis(tert-butyloxycarbonyl)-L-lysine dicyclohexylamine salt

N,N'-bis(tert-butyloxycarbonyl)-L-lysine dicyclohexylamine salt

Boc-Lys(Boc)-OH
2483-46-7

Boc-Lys(Boc)-OH

Conditions
ConditionsYield
With potassium hydrogensulfate In diethyl ether; water for 0.333333h; Product distribution / selectivity;100%
With citric acid In water; ethyl acetate at 0℃; for 0.5h;97%
With water In ethyl acetate
With hydrogenchloride In water; ethyl acetate
L-lysine
56-87-1

L-lysine

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

Boc-Lys(Boc)-OH
2483-46-7

Boc-Lys(Boc)-OH

Conditions
ConditionsYield
With sodium hydroxide In 1,4-dioxane97%
With sodium hydrogencarbonate In tetrahydrofuran; water at 30℃; for 24h; Inert atmosphere;92%
With sodium hydroxide In 1,4-dioxane; water at 20℃; for 12h;92%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

Boc-Lys-OH
13734-28-6

Boc-Lys-OH

Boc-Lys(Boc)-OH
2483-46-7

Boc-Lys(Boc)-OH

Conditions
ConditionsYield
With triethylamine In 1,4-dioxane; water for 18h; Cooling with ice;93%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

(S)-2-amino-6-(tert-butoxycarbonylamino)hexanoic acid
2418-95-3

(S)-2-amino-6-(tert-butoxycarbonylamino)hexanoic acid

Boc-Lys(Boc)-OH
2483-46-7

Boc-Lys(Boc)-OH

Conditions
ConditionsYield
With sodium hydroxide In water; tert-butyl alcohol at 20 - 40℃; for 16h;82%
Stage #1: di-tert-butyl dicarbonate; (S)-2-amino-6-(tert-butoxycarbonylamino)hexanoic acid With sodium hydroxide In tetrahydrofuran; water at 20℃; for 6h; pH=9 - 11;
Stage #2: With citric acid In water pH=4 - 5;
N-(tert-butyloxycarbonyl) azide
1070-19-5

N-(tert-butyloxycarbonyl) azide

L-Lysine hydrochloride
657-27-2, 10098-89-2

L-Lysine hydrochloride

Boc-Lys(Boc)-OH
2483-46-7

Boc-Lys(Boc)-OH

Conditions
ConditionsYield
With sodium carbonate
tert-butyl (quinolin-8-yl)carbonate
18595-55-6

tert-butyl (quinolin-8-yl)carbonate

L-lysine
56-87-1

L-lysine

Boc-Lys(Boc)-OH
2483-46-7

Boc-Lys(Boc)-OH

Conditions
ConditionsYield
With sodium hydroxide In N,N-dimethyl-formamide
L-lysine
56-87-1

L-lysine

tert-Butyl 4-nitrophenyl carbonate
13303-10-1

tert-Butyl 4-nitrophenyl carbonate

Boc-Lys(Boc)-OH
2483-46-7

Boc-Lys(Boc)-OH

Conditions
ConditionsYield
With sodium hydroxide In tert-butyl alcohol
With triethylamine
1,1-dimethylethyl 2,4,5-trichlorophenyl carbonate
16965-08-5

1,1-dimethylethyl 2,4,5-trichlorophenyl carbonate

L-Lysine hydrochloride
657-27-2, 10098-89-2

L-Lysine hydrochloride

Boc-Lys(Boc)-OH
2483-46-7

Boc-Lys(Boc)-OH

Conditions
ConditionsYield
With triethylamine In water; butan-1-ol
Nα,Nε-Di-tert.-butyloxycarbonyl-L-lysin-ethylester
99872-16-9

Nα,Nε-Di-tert.-butyloxycarbonyl-L-lysin-ethylester

Boc-Lys(Boc)-OH
2483-46-7

Boc-Lys(Boc)-OH

Conditions
ConditionsYield
With sodium hydroxide
tert-Butyl 4-nitrophenyl carbonate
13303-10-1

tert-Butyl 4-nitrophenyl carbonate

Boc-Lys(Boc)-OH
2483-46-7

Boc-Lys(Boc)-OH

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Py
2: aq. NaOH
View Scheme
L-lysine ethyl ester dihydrochloride
3844-53-9

L-lysine ethyl ester dihydrochloride

Boc-Lys(Boc)-OH
2483-46-7

Boc-Lys(Boc)-OH

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Py
2: aq. NaOH
View Scheme
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

Boc-Lys(Boc)-OH
2483-46-7

Boc-Lys(Boc)-OH

Conditions
ConditionsYield
Stage #1: L-Lysine hydrochloride With water at 35℃;
Stage #2: di-tert-butyl dicarbonate With sodium hydroxide In water at 30 - 50℃; for 2h; pH=> 8;
Nα,Nε-di-Boc-L-lysine p-nitrophenyl ester
2592-19-0

Nα,Nε-di-Boc-L-lysine p-nitrophenyl ester

Boc-Lys(Boc)-OH
2483-46-7

Boc-Lys(Boc)-OH

Conditions
ConditionsYield
With Cu(II)(2,6-bis(6-monoamino-β-cyclodextrinmethyl)pyridine) In acetonitrile at 25℃; pH=8.2; Kinetics; Reagent/catalyst;
di(succinimido) carbonate
74124-79-1

di(succinimido) carbonate

Boc-Lys(Boc)-OH
2483-46-7

Boc-Lys(Boc)-OH

N,N'-di-t-butyloxycarbonyl-(S)-lysine N-hydroxysuccinimide ester
30189-36-7

N,N'-di-t-butyloxycarbonyl-(S)-lysine N-hydroxysuccinimide ester

Conditions
ConditionsYield
With pyridine100%
2,3,4,5,6-pentafluorophenol
771-61-9

2,3,4,5,6-pentafluorophenol

Boc-Lys(Boc)-OH
2483-46-7

Boc-Lys(Boc)-OH

pentafluorophenyl N-α-N-ε-di-Boc-L-lysinate
85535-59-7

pentafluorophenyl N-α-N-ε-di-Boc-L-lysinate

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In ethyl acetate at 20℃; for 1h;100%
With dicyclohexyl-carbodiimide In dichloromethane at 25℃;92%
With dicyclohexyl-carbodiimide In 1,4-dioxane for 2h;86.5%
With dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 1.75h;
Boc-Lys(Boc)-OH
2483-46-7

Boc-Lys(Boc)-OH

N-hydroxysuccinimido diphenyl phosphate
75513-55-2

N-hydroxysuccinimido diphenyl phosphate

N,N'-di-t-butyloxycarbonyl-(S)-lysine N-hydroxysuccinimide ester
30189-36-7

N,N'-di-t-butyloxycarbonyl-(S)-lysine N-hydroxysuccinimide ester

Conditions
ConditionsYield
With pyridine100%
1,6-Hexanediamine
124-09-4

1,6-Hexanediamine

Boc-Lys(Boc)-OH
2483-46-7

Boc-Lys(Boc)-OH

Boc-L-Lys(Boc)-NH(CH2)6NH2

Boc-L-Lys(Boc)-NH(CH2)6NH2

Conditions
ConditionsYield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; benzotriazol-1-ol at 20℃; for 1h; Acylation;100%
Boc-Lys(Boc)-OH
2483-46-7

Boc-Lys(Boc)-OH

[5-[6-(2,6-diamino-hexanoylamino)-hexylcarbamoyl]-5-(9H-fluoren-9-ylmethoxycarbonylamino)-pentyl]-carbamic acid 9H-fluoren-9-ylmethyl ester

[5-[6-(2,6-diamino-hexanoylamino)-hexylcarbamoyl]-5-(9H-fluoren-9-ylmethoxycarbonylamino)-pentyl]-carbamic acid 9H-fluoren-9-ylmethyl ester

[5-{6-[2,6-bis-(2,6-bis-tert-butoxycarbonylamino-hexanoylamino)-hexanoylamino]-hexylcarbamoyl}-5-(9H-fluoren-9-ylmethoxycarbonylamino)-pentyl]-carbamic acid 9H-fluoren-9-ylmethyl ester

[5-{6-[2,6-bis-(2,6-bis-tert-butoxycarbonylamino-hexanoylamino)-hexanoylamino]-hexylcarbamoyl}-5-(9H-fluoren-9-ylmethoxycarbonylamino)-pentyl]-carbamic acid 9H-fluoren-9-ylmethyl ester

Conditions
ConditionsYield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; benzotriazol-1-ol at 20℃; for 1h; Acylation;100%
(S)-methyl 2-amino-6-(tert-butoxycarbonylamino)hexanoate
3017-32-1

(S)-methyl 2-amino-6-(tert-butoxycarbonylamino)hexanoate

Boc-Lys(Boc)-OH
2483-46-7

Boc-Lys(Boc)-OH

Boc-Lys(Boc)-Lys(Boc)-OMe

Boc-Lys(Boc)-Lys(Boc)-OMe

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 2.5h;100%
Boc-Lys(Boc)-OH
2483-46-7

Boc-Lys(Boc)-OH

C60H93N9O14S

C60H93N9O14S

C76H121N11O19S

C76H121N11O19S

Conditions
ConditionsYield
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 0 - 20℃;100%
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 0 - 20℃;0.270 g
Boc-Lys(Boc)-OH
2483-46-7

Boc-Lys(Boc)-OH

L-lysine dihydrochloride
657-26-1

L-lysine dihydrochloride

Conditions
ConditionsYield
With hydrogenchloride In 1,4-dioxane; methanol at 20℃; for 24h;100%
Boc-Lys(Boc)-OH
2483-46-7

Boc-Lys(Boc)-OH

2,6-Dichlor-N-phenylbenzimidchlorid
113055-87-1

2,6-Dichlor-N-phenylbenzimidchlorid

Nα,Nε-Bis(tert-butoxycarbonyl)-N-(2,6-dichlorbenzoyl)-N-phenyl-L-lysinamid
113035-36-2

Nα,Nε-Bis(tert-butoxycarbonyl)-N-(2,6-dichlorbenzoyl)-N-phenyl-L-lysinamid

Conditions
ConditionsYield
With triethylamine In acetone for 4h; Ambient temperature;99%
1-hydroxy-pyrrolidine-2,5-dione
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

Boc-Lys(Boc)-OH
2483-46-7

Boc-Lys(Boc)-OH

N,N'-di-t-butyloxycarbonyl-(S)-lysine N-hydroxysuccinimide ester
30189-36-7

N,N'-di-t-butyloxycarbonyl-(S)-lysine N-hydroxysuccinimide ester

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; Inert atmosphere;99%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃;88%
With dicyclohexyl-carbodiimide In tetrahydrofuran86%
Boc-Lys(Boc)-OH
2483-46-7

Boc-Lys(Boc)-OH

C20H29ClN4O2*2C2HF3O2

C20H29ClN4O2*2C2HF3O2

C36H57ClN6O7

C36H57ClN6O7

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 0 - 20℃; for 14.5h; Inert atmosphere;99%
Boc-Lys(Boc)-OH
2483-46-7

Boc-Lys(Boc)-OH

N-decyl-1-aminomethylnaphthalene hydrochloride
1558953-12-0

N-decyl-1-aminomethylnaphthalene hydrochloride

1-(N-(Nα,Nε-di-Boc-Lys)-N-decylamino)methylnaphthalene
1558953-40-4

1-(N-(Nα,Nε-di-Boc-Lys)-N-decylamino)methylnaphthalene

Conditions
ConditionsYield
Stage #1: Boc-Lys(Boc)-OH With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In chloroform; N,N-dimethyl-formamide at 0℃; for 0.0833333h;
Stage #2: N-decyl-1-aminomethylnaphthalene hydrochloride In chloroform; N,N-dimethyl-formamide at 0 - 20℃; for 24.5h;
98%
Boc-Lys(Boc)-OH
2483-46-7

Boc-Lys(Boc)-OH

(S)-2-amino-N-methoxy-N-methylpropanamide hydrochloride

(S)-2-amino-N-methoxy-N-methylpropanamide hydrochloride

di-tert-butyl ((S)-6-(((S)-1-(methoxy(methyl)amino)-1-oxopropan-2-yl)amino)-6-oxohexane-1,5-diyl)dicarbamate

di-tert-butyl ((S)-6-(((S)-1-(methoxy(methyl)amino)-1-oxopropan-2-yl)amino)-6-oxohexane-1,5-diyl)dicarbamate

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 N,N-dimethyl-formamide at 20℃; for 1.5h; Inert atmosphere;98%
Boc-Lys(Boc)-OH
2483-46-7

Boc-Lys(Boc)-OH

methyl iodide
74-88-4

methyl iodide

(+)-(S)-N2,N6-bis[(1,1-dimethylethoxy)carbonyl]-lysine methyl ester
2483-48-9

(+)-(S)-N2,N6-bis[(1,1-dimethylethoxy)carbonyl]-lysine methyl ester

Conditions
ConditionsYield
With potassium carbonate In ethyl acetate; N,N-dimethyl-formamide at 10 - 20℃; for 5h; Inert atmosphere;97%
Stage #1: Boc-Lys(Boc)-OH With caesium carbonate In tetrahydrofuran; water
Stage #2: methyl iodide In N,N-dimethyl-formamide for 2h;
65%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 2h;3 g
Boc-Lys(Boc)-OH
2483-46-7

Boc-Lys(Boc)-OH

N-hexyl-1-aminomethylbenzene hydrochloride
90389-37-0

N-hexyl-1-aminomethylbenzene hydrochloride

1-(N-(Nα,Nε-di-Boc-Lys)-N-hexylamino)methylbenzene
1558953-46-0

1-(N-(Nα,Nε-di-Boc-Lys)-N-hexylamino)methylbenzene

Conditions
ConditionsYield
Stage #1: Boc-Lys(Boc)-OH With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In chloroform; N,N-dimethyl-formamide at 0℃; for 0.0833333h;
Stage #2: N-hexyl-1-aminomethylbenzene hydrochloride In chloroform; N,N-dimethyl-formamide at 0 - 20℃; for 24.5h;
97%
Stage #1: Boc-Lys(Boc)-OH With N-ethyl-N,N-diisopropylamine In chloroform; N,N-dimethyl-formamide
Stage #2: With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate In chloroform; N,N-dimethyl-formamide
Stage #3: N-hexyl-1-aminomethylbenzene hydrochloride In chloroform; N,N-dimethyl-formamide at 0 - 20℃; for 24.5h;
beta-alanine methyl ester hydrochloride

beta-alanine methyl ester hydrochloride

Boc-Lys(Boc)-OH
2483-46-7

Boc-Lys(Boc)-OH

(S)-methyl 3-(2,6-bis(tert-butoxycarbonylamino)hexanamido)propanoate

(S)-methyl 3-(2,6-bis(tert-butoxycarbonylamino)hexanamido)propanoate

Conditions
ConditionsYield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In N,N-dimethyl-formamide97%
Boc-Lys(Boc)-OH
2483-46-7

Boc-Lys(Boc)-OH

methyl 3-aminopropanoate hydrochloride
3196-73-4

methyl 3-aminopropanoate hydrochloride

(S)-methyl 3-(2,6-bis(tert-butoxycarbonylamino)hexanamido)propanoate

(S)-methyl 3-(2,6-bis(tert-butoxycarbonylamino)hexanamido)propanoate

Conditions
ConditionsYield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In N,N-dimethyl-formamide97%
Boc-Lys(Boc)-OH
2483-46-7

Boc-Lys(Boc)-OH

(S)-3-(3-fluoro-4-morpholinophenyl)-5-((octylamino)methyl)oxazolidin-2-one

(S)-3-(3-fluoro-4-morpholinophenyl)-5-((octylamino)methyl)oxazolidin-2-one

di-tert-butyl ((5s)-6-(((3-(3-fluoro-4-morpholinophenyl)-2-oxooxazolidin-5-yl)methyl) (octyl)amino)-6-oxohexane-1,5-diyl)dicarbamate

di-tert-butyl ((5s)-6-(((3-(3-fluoro-4-morpholinophenyl)-2-oxooxazolidin-5-yl)methyl) (octyl)amino)-6-oxohexane-1,5-diyl)dicarbamate

Conditions
ConditionsYield
Stage #1: (S)-3-(3-fluoro-4-morpholinophenyl)-5-((octylamino)methyl)oxazolidin-2-one With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In chloroform; N,N-dimethyl-formamide at 0℃; for 0.0833333h;
Stage #2: Boc-Lys(Boc)-OH In chloroform; N,N-dimethyl-formamide at 0 - 20℃; for 24.5h;
96.9%
Boc-Lys(Boc)-OH
2483-46-7

Boc-Lys(Boc)-OH

(S)-5-((decylamino)methyl)-3-(3-fluoro-4-morpholinophenyl)oxazolidin-2-one

(S)-5-((decylamino)methyl)-3-(3-fluoro-4-morpholinophenyl)oxazolidin-2-one

di-tert-butyl ((5s)-6-(decyl((3-(3-fluoro-4-morpholinophenyl)-2-oxooxazolidin-5-yl)methyl)amino)-6-oxohexane-1,5-diyl)dicarbamate

di-tert-butyl ((5s)-6-(decyl((3-(3-fluoro-4-morpholinophenyl)-2-oxooxazolidin-5-yl)methyl)amino)-6-oxohexane-1,5-diyl)dicarbamate

Conditions
ConditionsYield
Stage #1: (S)-5-((decylamino)methyl)-3-(3-fluoro-4-morpholinophenyl)oxazolidin-2-one With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In chloroform; N,N-dimethyl-formamide at 0℃; for 0.0833333h;
Stage #2: Boc-Lys(Boc)-OH In chloroform; N,N-dimethyl-formamide at 0 - 20℃; for 24.5h;
96.7%
Boc-Lys(Boc)-OH
2483-46-7

Boc-Lys(Boc)-OH

1-aminooctadecane
124-30-1

1-aminooctadecane

((S)-5-tert-Butoxycarbonylamino-5-octadecylcarbamoyl-pentyl)-carbamic acid tert-butyl ester

((S)-5-tert-Butoxycarbonylamino-5-octadecylcarbamoyl-pentyl)-carbamic acid tert-butyl ester

Conditions
ConditionsYield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 20℃; for 24h; Inert atmosphere;96%
With 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide In chloroform at 0℃;
Boc-Lys(Boc)-OH
2483-46-7

Boc-Lys(Boc)-OH

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

N,O-dimethylhydroxylamine*hydrochloride

[5-tert-butoxycarbonylamino-5-(methoxy-methyl-carbamoyl)-pentyl]-carbamic acid tert-butyl ester
761456-85-3

[5-tert-butoxycarbonylamino-5-(methoxy-methyl-carbamoyl)-pentyl]-carbamic acid tert-butyl ester

Conditions
ConditionsYield
Stage #1: Boc-Lys(Boc)-OH 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;
96%
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In dichloromethane at 20℃; for 1h;94%
Boc-Lys(Boc)-OH
2483-46-7

Boc-Lys(Boc)-OH

methyl 6-O-trityl-α-D-glucopyranoside
18311-26-7

methyl 6-O-trityl-α-D-glucopyranoside

methyl 2,3,4-tri-O-α,Nε-bis(t-butoxycarbonyl)-L-lysyl>-6-O-triphenylmethyl-α-D-glucopyranoside

methyl 2,3,4-tri-O-α,Nε-bis(t-butoxycarbonyl)-L-lysyl>-6-O-triphenylmethyl-α-D-glucopyranoside

Conditions
ConditionsYield
With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane 1) 0 deg C, 2 h, 2) r.t., overnight;95%
C35H63N11O14
192873-60-2

C35H63N11O14

Boc-Lys(Boc)-OH
2483-46-7

Boc-Lys(Boc)-OH

C51H91N13O19
1402052-18-9

C51H91N13O19

Conditions
ConditionsYield
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; Inert atmosphere;95%
Boc-Lys(Boc)-OH
2483-46-7

Boc-Lys(Boc)-OH

C94H167ClN6O19Si4

C94H167ClN6O19Si4

C110H195ClN8O24Si4

C110H195ClN8O24Si4

Conditions
ConditionsYield
Stage #1: Boc-Lys(Boc)-OH With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0℃; for 0.25h;
Stage #2: C94H167ClN6O19Si4 In N,N-dimethyl-formamide at 0 - 20℃;
95%
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide
Boc-Lys(Boc)-OH
2483-46-7

Boc-Lys(Boc)-OH

C17H41N9O2

C17H41N9O2

C41H89N17O6

C41H89N17O6

Conditions
ConditionsYield
Stage #1: Boc-Lys(Boc)-OH; C17H41N9O2 With diisopropyl-carbodiimide In methanol at 20℃; for 0.25h;
Stage #2: With trifluoroacetic acid In methanol; dichloromethane for 2h;
95%
(1S,2S,5R,6S)-2-aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid dimethyl ester hydrochloride

(1S,2S,5R,6S)-2-aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid dimethyl ester hydrochloride

Boc-Lys(Boc)-OH
2483-46-7

Boc-Lys(Boc)-OH

(1S,2S,5R,6S)-2-[(2'S)-(2',6'-bis(tert-butoxycarbonyl)amino)hexanoyl]aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid dimethyl ester
441775-51-5

(1S,2S,5R,6S)-2-[(2'S)-(2',6'-bis(tert-butoxycarbonyl)amino)hexanoyl]aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid dimethyl ester

Conditions
ConditionsYield
With dmap; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine In dichloromethane at 20℃;94%
Boc-Lys(Boc)-OH
2483-46-7

Boc-Lys(Boc)-OH

Propargylamine
2450-71-7

Propargylamine

(S)-di-(tert-butyl) 6-oxo-6-(prop-2-ynylamino)hexane-1,5-diyldicarbamate
478843-83-3

(S)-di-(tert-butyl) 6-oxo-6-(prop-2-ynylamino)hexane-1,5-diyldicarbamate

Conditions
ConditionsYield
Stage #1: Boc-Lys(Boc)-OH With 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide In dichloromethane for 0.166667h; Cooling with ice;
Stage #2: Propargylamine With triethylamine In dichloromethane
94%
Stage #1: Boc-Lys(Boc)-OH With 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 0.5h;
Stage #2: Propargylamine With triethylamine In dichloromethane at 0℃;
94%
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 24.5h; Inert atmosphere; Cooling with ice;64%

2483-46-7Relevant articles and documents

Two-component dendritic gel: Effect of stereochemistry on the supramolecular chiral assembly

Hirst, Andrew R.,Smith, David K.,Feiters, Martin C.,Geurts, Huub P. M.

, p. 5901 - 5910 (2004)

The self-assembly of diaminododecane solubilised by four different stereoisomeric dendritic peptides to form gel-phase materials in toluene was investigated. The second generation dendritic peptides were based on D- and L-lysine building blocks, and each contained three chiral centres. By designing dendritic peptides in which the configurations of the chiral centres were modified, and applying them as gelator units, the assembly of stereoisomers could be investigated. In all cases, the self-assembly of gelator units resulted in macroscopic gelation. However, the degree of structuring was modulated by the stereoisomers employed, an effect which changed the morphology and macroscopic behavior of the self-assembled state. Enantiomeric (L,L,L or D,D,D) gelator units formed fibrous molecular assemblies, whilst the racemic gel (50% L,L,L: 50% D,D,D) formed a flat structure with a "woven" appearance. Gelator units based on L,D,D or D,L,L dendritic peptides also formed fibrous assemblies, but small-angle X-ray scattering indicated significant morphological differences were caused by the switch in chirality. Furthermore, the macroscopic stability of the gel was diminished when these peptides were compared with their L,L,L or D,D,D analogues. In this paper it is clearly shown that individual stereocentres, on the molecular level, are directly related to the helicity within the fibre. It is argued that the chirality controls the pattern of hydrogen bonding within the assembly, and hence determines the extent of fibre formation and the macroscopic gel strength.

Synthesis and antibacterial bioactivities of cationic deacetyl linezolid amphiphiles

Bai, Peng-Yan,Qin, Shang-Shang,Chu, Wen-Chao,Yang, Yi,Cui, De-Yun,Hua, Yong-Gang,Yang, Qian-Qian,Zhang, En

, p. 925 - 945 (2018)

Bacterial infections cause various life-threatening diseases and have become a serious public health problem due to the emergence of drug-resistant strains. Thus, novel antibiotics with excellent antibacterial activity and low cytotoxicity are urgently needed. Here, three series of novel cationic deacetyl linezolid amphiphiles bearing one lipophilic alkyl chain and one non-peptidic amide bond were synthesized and tested for antimicrobial activities. Several compounds showed excellent antibacterial activity toward drug-sensitive bacteria such as gram-negative bacteria Escherichia coli (E. coli), Salmonella enterica (S. enterica) and gram-positive Staphylococcus aureus (S. aureus), Enterococcus faecalis (E. faecalis). Moreover, these amphiphilic molecules also exhibited strong activity against drug-resistant species such as methicillin-resistant S. aureus (MRSA), KPC (Klebsiella pneumoniae carbapenemase) and NDM-1 (New Delhi metallo-β-lactamase 1) producing carbapenem-resistant Enterobacteriaceae (CRE). For example, the MICs (minimum inhibitory concentrations) of the best compound 6e, ranged from 2 to 16 μg/mL and linezolid ranged from 2 to >64 μg/mL against these strains. Therefore, 6e is a broad-spectrum antimicrobial compound that may be a suitable lead as an antibiotic. The molecule 6e were found to function primarily by permeabilization and depolarization of bacterial membranes. Importantly, bacterial resistance against compound 6e was difficult to induce, and 6e was stable under plasma conditions and showed suitable activity in mammalian plasma. Thus, these compounds can be further developed into a potential new class of broad-spectrum antibiotics.

Photocleavable antimicrobial peptide mimics for precluding antibiotic resistance

Feng, Yang,Zhang, Yang-Yang,Li, Ke,Tian, Na,Wang, Wei-Bo,Zhou, Qian-Xiong,Wang, Xue-Song

, p. 3192 - 3195 (2018)

Cationic amphiphiles featuring a lysine-based hydrophilic moiety, an alkyl chain-based hydrophobic moiety, and an o-nitrobenzyl group-based linker were constructed facilely, which show alkyl chain-dependent antibacterial activity against both Gram-positive and Gram-negative bacteria, low cytotoxicity toward mammalian cells, and UV-cleavable properties, representing a novel type of environmental accumulation-free antimicrobial peptide mimic.

Synthesis and evaluation of a bis-3-chloropiperidine derivative incorporating an anthraquinone pharmacophore

Zuravka, Ivonne,Sosic, Alice,Gatto, Barbara,G?ttlich, Richard

, p. 4606 - 4609 (2015)

With the aim to attain an alkylating agent with enhanced DNA-affinity, we have successfully synthesised lysine-linked bis-3-chloropiperidine 1 bearing an anthraquinone moiety known to bind double-stranded DNA. Consistent with our expectations, compound 1 appears to intercalate into the DNA double helix, which can be observed by conformational changes of plasmid DNA suggesting alkylation and intercalation-induced DNA unwinding. The results of this work can provide a meaningful starting point for investigating the molecular mechanism of action of this novel DNA alkylating conjugate 1 with improved affinity for DNA.

Appended Aromatic Moieties in Flexible Bis-3-chloropiperidines Confer Tropism against Pancreatic Cancer Cells

Carraro, Caterina,Helbing, Tim,Francke, Alexander,Zuravka, Ivonne,Sosic, Alice,De Franco, Michele,Gandin, Valentina,Gatto, Barbara,G?ttlich, D. Richard

, p. 860 - 868 (2020/12/07)

Nitrogen mustards (NMs) are an old but still largely diffused class of anticancer drugs. However, spreading mechanisms of resistance undermine their efficacy and therapeutic applicability. To expand their antitumour value, we developed bis-3-chloropiperidines (B-CePs), a new class of mustard-based alkylating agent, and we recently reported the striking selectivity for BxPC-3 pancreatic tumour cells of B-CePs bearing aromatic moieties embedded in the linker. In this study, we demonstrate that such tropism is shared by bis-3-chloropiperidines bearing appended aromatic groups in flexible linkers, whereas esters substituted by aliphatic groups or by efficient DNA-interacting groups are potent but nonselective cytotoxic agents. Besides, we describe how the critical balance between water stability and DNA reactivity can affect the properties of bis-3-chloropiperidines. Together, these findings support the exploitation of B-CePs as potential antitumour clinical candidates.

Rhamnolipid inspired lipopeptides effective in preventing adhesion and biofilm formation of Candida albicans

Jovanovic, Milos,Radivojevic, Jelena,O'Connor, Kevin,Blagojevic, Stevan,Begovic, Biljana,Lukic, Vera,Nikodinovic-Runic, Jasmina,Savic, Vladimir

supporting information, p. 209 - 217 (2019/03/23)

Rhamnolipids are biodegradable low toxic biosurfactants which exert antimicrobial and anti-biofilm properties. They have attracted much attention recently due to potential applications in areas of bioremediation, therapeutics, cosmetics and agriculture, however, the full potential of these versatile molecules is yet to be explored. Based on the facts that many naturally occurring lipopeptides are potent antimicrobials, our study aimed to explore the potential of replacing rhamnose in rhamnolipids with amino acids thus creating lipopeptides that would mimic or enhance properties of the parent molecule. This would allow not only for more economical and greener production but also, due to the availability of structurally different amino acids, facile manipulation of physico-chemical and biological properties. Our synthetic efforts produced a library of 43 lipopeptides revealing biologically more potent molecules. The structural changes significantly increased, in particular, anti-biofilm properties against Candida albicans, although surface activity of the parent molecule was almost completely abolished. Our findings show that the most active compounds are leucine derivatives of 3-hydroxy acids containing benzylic ester functionality. The SAR study demonstrated a further increase in activity with aliphatic chain elongation. The most promising lipopeptides 15, 23 and 36 at 12.5 μg/mL concentration allowed only 14.3%, 5.1% and 11.2% of biofilm formation, respectively after 24 h. These compounds inhibit biofilm formation by preventing adhesion of C. albicans to abiotic and biotic surfaces.

AMPHIPHILIC CONJUGATES OF TOBRAMYCIN LINKED TO A LYSINE-BASED PEPTOID MIMIC VIA A TETHER

-

Page/Page column 24, (2018/11/22)

Amphiphilic conjugates of tobramycin linked to a lysine-based peptoid mimic via a tether are disclosed. Said lysine-based peptoid mimics comprise a positively-charged L-lysine, a hydrophobic aromatic core and an alkylene tether assembled through a tertiary amide linkage. Optimization of the resulting conjugate is provided using a C12 alkylene tether. These conjugates have utility as antibacterial agents, in particular when used in conjunction with another antibacterial agent (such as rifampicin or minocycline), where the combination results in a synergistic activity against drug-resistant bacteria (in particular extensively drug-resistant P. aeruginosa). As a result, these conjugates provide for effective antibiotic adjuvants that help overcome resistance of Gram-negative bacteria to antibiotics.

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