CAS 103321-55-7

FMOC-CYS(BZL)-CL

Description:

FMOC-CYS(BZL)-CL, also known as 9-fluorenylmethoxycarbonyl-L-cysteine (benzyl) chloride, is a chemical compound commonly used in peptide synthesis and biochemistry. It features a fluorenylmethoxycarbonyl (FMOC) protecting group, which is widely utilized for the protection of amino groups during peptide synthesis due to its stability under basic conditions and ease of removal under mild acidic conditions. The presence of the benzyl group (BZL) on the cysteine residue enhances the compound's hydrophobicity and can influence the folding and stability of peptides. The chloride (CL) indicates that this compound is likely in its activated form, facilitating coupling reactions with other amino acids. FMOC-CYS(BZL)-CL is typically handled under controlled conditions due to its reactivity and potential toxicity. Its applications extend to the synthesis of peptides that require specific modifications, particularly those involving cysteine, which plays a crucial role in forming disulfide bonds in protein structures. Proper storage and handling are essential to maintain its integrity and efficacy in synthetic applications.

Formula: C₂₅H₂₂ClNO₃S

InChI: InChI=1S/C25H22ClNO3S/c26-24(28)23(16-31-15-17-8-2-1-3-9-17)27-25(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,27,29)/t23-/m0/s1

InChI key: InChIKey=SROXPZPJVPCTHD-QHCPKHFHSA-N

SMILES: C(OC(N[C@@H](CSCC1=CC=CC=C1)C(Cl)=O)=O)C2C=3C(C=4C2=CC=CC4)=CC=CC3

Synonyms:

• Carbamic acid, [(1S)-2-chloro-2-oxo-1-[[(phenylmethyl)thio]methyl]ethyl]-, 9H-fluoren-9-ylmethyl ester
• Carbamic acid, [2-chloro-2-oxo-1-[[(phenylmethyl)thio]methyl]ethyl]-, 9H-fluoren-9-ylmethyl ester, (S)-
• Fmoc-S-Benzyl-L-Cysteinyl Chloride
• NALPHA-9-Fluorenylmethoxycarbonyl-S-benzyl-L-cysteinyl chloride
• FMOC-CYS(BZL)-CL
• Carbamic acid, [(1S)-2-chloro-2-oxo-1-[[(phenylmethyl)thio]methyl]ethyl]-, 9H-fluoren-9-ylmethyl ester (9CI)