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467154

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

Name: <I>N</I>-(<I>tert</I>-Butoxycarbonyl)-<SC>L</SC>-cysteine methyl ester
Brand: ALDRICH

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

MDL number:

MFCD00799495

UNSPSC Code:

12352209

eCl@ss:

32160406

PubChem Substance ID:

24870386

NACRES:

NA.22

product name

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

Quality Level

100

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

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

Related Categories

Amino Acids, Resins & Reagents for Peptide Synthesis

Thiols

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.

WGK

WGK 3

Flash Point(F)

closed cup

Flash Point(C)

closed cup

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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Methods for converting cysteine to dehydroalanine on peptides and proteins.

Chalker J M, et al.

Chemical Science, 2(9), 1666-1676 (2011)

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)

S-(3-Aminobenzanthron-2-yl)cysteine in the globin of rats as a novel type of adduct and possible biomarker of exposure to 3-nitrobenzanthrone, a potent environmental carcinogen.

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

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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