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96840

Sigma-Aldrich

H-Lys(Z)-OH

≥99.0% (NT)

Synonym(s):

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

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About This Item

Linear Formula:
C6H5CH2OOCNH(CH2)4CH(NH2)COOH
CAS Number:
1155-64-2
Molecular Weight:
280.32
Beilstein/REAXYS Number:
2222482
EC Number:
214-585-7
MDL number:
MFCD00002638
UNSPSC Code:
12352200
eCl@ss:
32160406
PubChem Substance ID:
57653788
NACRES:
NA.22

Quality Level

200

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)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Boc-Lys(Fmoc)-OH ≥99.0% (sum of enantiomers, TLC)

Sigma-Aldrich

15435

Boc-Lys(Fmoc)-OH

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.
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
J Zheng et al.
Biotechnology progress, 15(4), 763-767 (1999-08-12)
Microspheres were formed from blends of the biodegradable polymer poly(DL-lactic-co-glycolic acid) (PLGA) together with poly(epsilon-CBZ-L-lysine) (PCBZL) by a double-emulsification/solvent evaporation technique. The size of the microspheres formed by this method was dependent both on the total concentration of the polymers
Christopher D Reinkemeier et al.
Cell, 184(19), 4886-4903 (2021-08-26)
Engineering new functionality into living eukaryotic systems by enzyme evolution or de novo protein design is a formidable challenge. Cells do not rely exclusively on DNA-based evolution to generate new functionality but often utilize membrane encapsulation or formation of membraneless

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