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96840

Sigma-Aldrich

H-Lys(Z)-OH

≥99.0% (NT)

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Synonym(s):
Nε-Z-L-lysine, N6-Carbobenzyloxy-L-lysine
Linear Formula:
C6H5CH2OOCNH(CH2)4CH(NH2)COOH
CAS Number:
Molecular Weight:
280.32
Beilstein/REAXYS Number:
2222482
EC Number:
MDL number:
eCl@ss:
32160406
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

≥99.0% (NT)

form

powder

optical activity

[α]20/D +15.5±1°, c = 1% in 1 M HCl

reaction suitability

reaction type: solution phase peptide synthesis

mp

259 °C (dec.) (lit.)

application(s)

peptide synthesis

SMILES string

N[C@@H](CCCCNC(=O)OCc1ccccc1)C(O)=O

InChI

1S/C14H20N2O4/c15-12(13(17)18)8-4-5-9-16-14(19)20-10-11-6-2-1-3-7-11/h1-3,6-7,12H,4-5,8-10,15H2,(H,16,19)(H,17,18)/t12-/m0/s1

InChI key

CKGCFBNYQJDIGS-LBPRGKRZSA-N

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1 of 4

This Item
154569688596890
vibrant-m

96840

H-Lys(Z)-OH

vibrant-m

15456

Boc-Lys-OH

vibrant-m

96885

Z-Lys(Z)-OSu

vibrant-m

96890

H-Lys(Z)-OMe hydrochloride

form

powder

form

solid

form

powder

form

powder

mp

259 °C (dec.) (lit.)

mp

~205 °C (dec.) (lit.)

mp

-

mp

-

optical activity

[α]20/D +15.5±1°, c = 1% in 1 M HCl

optical activity

[α]20/D +4.6±0.5°, c = 2% in H2O

optical activity

-

optical activity

[α]20/D +14.5±0.5°, c = 2% in H2O

Quality Level

200

Quality Level

200

Quality Level

100

Quality Level

100

reaction suitability

reaction type: solution phase peptide synthesis

reaction suitability

reaction type: Boc solid-phase peptide synthesis

reaction suitability

reaction type: solution phase peptide synthesis

reaction suitability

reaction type: solution phase peptide synthesis

General description

H-Lys(Z)-OH also known as N6-carbobenzyloxy-L-lysine, commonly used as a reagent in the synthesis of peptides.

Application

H-Lys(Z)-OH serves as a reactant for the synthesis of various peptides such as boc-Glu(OBzl)-Lys(Z)-OH and tert-butyl-6-(((benzyloxy)carbonyl)amino)-2-bromohexanoate. Additionally, it is used in the Fuchs-Farthing method to synthesize lysine NCA, which is a block copolymer.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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Sigma-Aldrich

15435

Boc-Lys(Fmoc)-OH

Poly (ethylene glycol)-b-poly (lysine) copolymer bearing nitroaromatics for hypoxia-sensitive drug delivery
T Thambi
Acta Biomaterialia, 29, 261-270 (2016)
Preparation of protected peptide intermediates for a synthesis of the ovine pituitary growth hormone sequence 96-135
SS Wang
The Journal of Organic Chemistry, 40, 1227-1234 (1975)
Synthesis and characterization of pH-sensitive, biotinylated MRI contrast agents and their conjugates with avidin
SM Vibhute
Organic & Biomolecular Chemistry, 11, 1294-1305 (2013)
J Zheng et al.
Biotechnology progress, 16(2), 254-257 (2000-04-08)
Poly(epsilon-CBZ-L-lysine) can be mixed with biodegradable polymers such as poly(D,L-lactic-co-glycolic acid) or poly(L-lactic acid) and formed into films, foams, or microspheres. Surface amino groups may then be deprotected with acid or lithium/liquid ammonia. The amino groups serve as a method
R L Hanson et al.
Applied microbiology and biotechnology, 37(5), 599-603 (1992-08-01)
Biotransformations were developed to oxidize N epsilon-carbobenzoxy(CBZ)-L-lysine and to reduce the product keto acid to L-CBZ-oxylysine. Lysyl oxidase (L-lysine: O2 oxidoreductase, EC 1.4.3.14) from Trichoderma viride was relatively specific for L-lysine and had very low activity with N epsilon-substituted derivatives.

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