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Fmoc-L-Cys(Cam)-OH
Chemical name: N-(((9H-fluoren-9-yl)methoxy)carbonyl)-S-(2-amino-2-oxoethyl)-L-cysteine // Synonyms: Fmoc-Cys(Cam)-OH, Fmoc-L-Cys(carboxamidomethyl)-OH, N-alpha-Fmoc-S-methylcarboxamide-L-cysteine
- Product code:FAA9090
- CAS No.:1443324-12-6
- Formula:C20H20N2O5S
- Molecular weight:400.45 g/mol
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description
Typically, for protein sequencing, cysteine residues are derivatized with iodoacetamide prior to enzymatic digestion and MS analysis of the peptide fragments. Thus, Cys(Cam) containing peptides are required as standards for MS quantitation of proteins. This building block enables Fmoc SPPS of reference peptides containing Cys(Cam) without the need for post-assembly manipulations. Fmoc-L-Cys(Cam)-OH is compatible to TFA and piperidine treatments.
references
Interaction of halogenacetates and SH compounds: The reaction of halogenacetic acids with glutathione and cysteine. The mechanism of iodoacetate poisoning of glyoxalase; F. Dickens; Biochemical Journal 1933; 27: 1141-1151. https://doi.org/10.1042/bj0271141
The reaction of iodoacetate and of iodoacetamide with various sulfhydryl groups, with urease, and with yeast preparations; C. V. Smythe; Journal of Biological Chemistry 1936; 114: 601-612. https://doi.org/10.1016/S0021-9258(18)74789-3
The absolute quantification strategy: a general procedure for the quantification of proteins and post-translational modifications; D. S. Kirkpatrick, S. A. Gerber, S. P. Gygi; Methods 2005; 35: 265-273. https://doi.org/https://doi.org/10.1016/j.ymeth.2004.08.018
Lysine-Targeting Reversible Covalent Inhibitors with Long Residence Time; R. M. Reja, W. Wang, Y. Lyu, F. Haeffner, J. Gao; Journal of the American Chemical Society 2022; 144: 1152-1157. https://doi.org/10.1021/jacs.1c12702
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Our building block Fmoc-L-Cys(Cam)-OH enables peptides resembling reduced and carbamido-methylated protein fragments by standard S
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