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Merck

96840

Sigma-Aldrich

H-Lys(Z)-OH

≥99.0% (NT), for peptide synthesis

Sinónimos:

Nε-Z-L-lysine, N6-Carbobenzyloxy-L-lysine

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About This Item

Fórmula lineal:
C6H5CH2OOCNH(CH2)4CH(NH2)COOH
Número de CAS:
Peso molecular:
280.32
Beilstein/REAXYS Number:
2222482
EC Number:
MDL number:
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
NACRES:
NA.22

product name

H-Lys(Z)-OH, ≥99.0% (NT)

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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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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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.
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

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