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47603

Sigma-Aldrich

Fmoc-Cys(Acm)-OH

≥95.0% (sum of enantiomers, HPLC)

Synonym(s):

Nα-Fmoc-S-acetaminomethyl-L-cysteine

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About This Item

Empirical Formula (Hill Notation):
C21H22N2O5S
CAS Number:
86060-81-3
Molecular Weight:
414.47
Beilstein:
4725388
MDL number:
MFCD00038769
UNSPSC Code:
12352200
PubChem Substance ID:
57651035
NACRES:
NA.26

Assay

≥95.0% (sum of enantiomers, HPLC)

optical activity

[α]/D -33.0±2.0°, c = 1 in methanol

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

application(s)

peptide synthesis

functional group

Fmoc

storage temp.

2-8°C

SMILES string

CC(=O)NCSC[C@H](NC(=O)OCC1c2ccccc2-c3ccccc13)C(O)=O

InChI

1S/C21H22N2O5S/c1-13(24)22-12-29-11-19(20(25)26)23-21(27)28-10-18-16-8-4-2-6-14(16)15-7-3-5-9-17(15)18/h2-9,18-19H,10-12H2,1H3,(H,22,24)(H,23,27)(H,25,26)/t19-/m0/s1

InChI key

CSMYOORPUGPKAP-IBGZPJMESA-N

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Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
BCCC4135
BCBZ5410
BCBV7820
BCBQ0491V
BCBP2814V

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Enrica Calce et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 24(23), 6231-6238 (2018-02-20)
An efficient and rapid procedure for synthesizing S-linked glycopeptides is reported. The approach uses activated molecular sieves as a base to promote the selective S-alkylation of readily prepared cysteine-containing peptides, upon reaction of appropriate glycosyl halides. Considering the very mild
Kusum Vats et al.
Journal of peptide science : an official publication of the European Peptide Society, 25(7), e3192-e3192 (2019-07-17)
The present study describes modification of asparagine-glycine-arginine (NGR) peptide at N-terminally and C-terminally by introduction of a tridentate chelating scaffold via click chemistry reaction. The N-terminal and C-terminal modified peptides were radiometalated with [99m Tc(CO)3 ]+ precursor. The influence of
S N McCurdy
Peptide research, 2(1), 147-152 (1989-01-01)
Fmoc-Cys(t-Bu)-OH, Fmoc-Cys(Acm)-OH, and Fmoc-Cys(Trt)-OH exhibit excellent synthesis characteristics when used in Fmoc solid phase peptide synthesis on the Applied Biosystems Model 431A peptide synthesizer. The actual 5% scavenger mixture will vary according to the particular amino acid residues present. As
Emma J Ste Marie et al.
Journal of peptide science : an official publication of the European Peptide Society, 24(11), e3130-e3130 (2018-10-26)
Triisopropylsilane (TIS), a hindered hydrosilane, has long been utilized as a cation scavenger for the removal of amino acid protecting groups during peptide synthesis. However, its ability to actively remove S-protecting groups by serving as a reductant has largely been
Fan Gao et al.
Small (Weinheim an der Bergstrasse, Germany), 14(37), e1802403-e1802403 (2018-08-22)
Chemotherapy is well recognized to induce immune responses during some chemotherapeutic drugs-mediated tumor eradication. Here, a strategy involving blocking programmed cell death protein 1 (PD-1) to enhance the chemotherapeutic effect of a doxorubicin nanoprodrug HA-Psi-DOX is proposed and the synergetic

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