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Sigma-Aldrich

H-Lys(Z)-OH

≥99.0% (NT), for peptide synthesis

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Synonym(s):
Nε-Z-L-lysine, N6-Carbobenzyloxy-L-lysine
Linear Formula:
C6H5CH2OOCNH(CH2)4CH(NH2)COOH
CAS Number:
1155-64-2
Molecular Weight:
280.32
Beilstein:
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.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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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)
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
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