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Merck
CN

467154

N-(tert-Butoxycarbonyl)-L-cysteine methyl ester

97%, for peptide synthesis

Synonym(s):

N-Boc-L-cysteine methyl ester

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About This Item

Linear Formula:
HSCH2CH[NHCO2C(CH3)3]CO2CH3
CAS Number:
55757-46-5
Molecular Weight:
235.30
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
24870386
NACRES:
NA.22
MDL number:
MFCD00799495

Key Documents

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Product Name

N-(tert-Butoxycarbonyl)-L-cysteine methyl ester, 97%

SMILES string

COC(=O)[C@H](CS)NC(=O)OC(C)(C)C

InChI

1S/C9H17NO4S/c1-9(2,3)14-8(12)10-6(5-15)7(11)13-4/h6,15H,5H2,1-4H3,(H,10,12)/t6-/m0/s1

InChI key

NJGIAKIPSDCYAC-LURJTMIESA-N

assay

97%

form

liquid

optical activity

[α]22/D +21°, c = 7.5 in chloroform

reaction suitability

reaction type: solution phase peptide synthesis

refractive index

n20/D 1.475 (lit.)

bp

214 °C (lit.)

density

1.143 g/mL at 25 °C (lit.)

application(s)

peptide synthesis

Quality Level

100

Related Categories

Application

N-(tert-Butoxycarbonyl)-L-cysteine methyl ester is an N-terminal protected reagent that can be used in the synthesis of peptides and proteins containing cysteine residues, which can further be converted to dehydroalanine.

Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

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Certificates of Analysis (COA)

Lot/Batch Number
MKCX4569
MKCS6860
MKCQ4295
MKCN4916
MKCL9591

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Igor Linhart et al.
Archives of toxicology, 91(10), 3317-3325 (2017-03-12)
3-Nitrobenzanthrone (3-NBA), a potent environmental mutagen and carcinogen, is known to be activated in vivo to 3-benzanthronylnitrenium ion which forms both NH and C2-bound adducts with DNA and also reacts with glutathione giving rise to urinary 3-aminobenzanthron-2-ylmercapturic acid. In this
Inactivation of NF-κB components by covalent binding of (−)-dehydroxymethylepoxyquinomicin to specific cysteine residues.
Yamamoto M, et al.
Journal of Medicinal Chemistry, 51(18), 5780-5788 (2008)
Methods for converting cysteine to dehydroalanine on peptides and proteins.
Chalker J M, et al.
Chemical Science, 2(9), 1666-1676 (2011)
An insight into the radical thiol/yne coupling: the emergence of arylalkyne-tagged sugars for the direct photoinduced glycosylation of cysteine-containing peptides.
Minozzi M, et al.
The Journal of Organic Chemistry, 76(2), 450-459 (2010)

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