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CAS 53298-33-2

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Fmoc-Cys(Bzl)-OH

Description:
Fmoc-Cys(Bzl)-OH, or 9-fluorenylmethoxycarbonyl-L-cysteine (benzyl) is a protected amino acid commonly used in peptide synthesis. It features a fluorenylmethoxycarbonyl (Fmoc) group, which serves as a protective group for the amino functionality, allowing for selective reactions during peptide assembly. The presence of the benzyl (Bzl) side chain on the cysteine residue provides additional steric bulk and can influence the peptide's folding and stability. This compound is typically white to off-white in appearance and is soluble in organic solvents such as dimethylformamide (DMF) and dimethyl sulfoxide (DMSO), but less soluble in water. The Fmoc group can be removed under basic conditions, facilitating the coupling of this amino acid into growing peptide chains. Its unique structure allows for the incorporation of cysteine into peptides, which can form disulfide bonds, crucial for the stability and functionality of many proteins. Overall, Fmoc-Cys(Bzl)-OH is a valuable building block in the field of synthetic chemistry and biochemistry.
Formula:C25H23NO4S
InChI:InChI=1/C25H23NO4S/c27-24(28)23(16-31-15-17-8-2-1-3-9-17)26-25(29)30-14-22-20-12-6-4-10-18(20)19-11-5-7-13-21(19)22/h1-13,22-23H,14-16H2,(H,26,29)(H,27,28)/t23-/m0/s1
SMILES:c1ccc(cc1)CSC[C@@H](C(=O)O)N=C(O)OCC1c2ccccc2c2ccccc12
Synonyms:
  • S-benzyl-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-cysteine
  • N-Fmoc-S-(phenylmethyl)-L-cysteine
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