Description

Fmoc-alpha-Me-L-Cys(Trt)-OH (CAS No. 725728-43-8) is a high-purity, protected amino acid derivative widely utilized in solid-phase peptide synthesis (SPPS). This compound features an Fmoc (9-fluorenylmethoxycarbonyl) protecting group for the α-amine and a Trt (triphenylmethyl) protecting group for the thiol functionality, ensuring selective deprotection during peptide assembly. With the molecular formula C₃₈H₃₃NO₄S and a molecular weight of 599.74 g/mol, it is specifically designed for the incorporation of α-methyl-L-cysteine residues into peptide chains, enhancing stability and conformational control. Ideal for researchers requiring precise modifications, this product is rigorously tested via HPLC and NMR to guarantee ≥95% purity, making it suitable for demanding applications in pharmaceutical development and biochemical research.

Properties

• CAS Number: 725728-43-8
• Complexity: 887
• IUPAC Name: (2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-2-methyl-3-tritylsulfanyl-propanoic acid
• InChI: InChI=1S/C38H33NO4S/c1-37(35(40)41,39-36(42)43-25-34-32-23-13-11-21-30(32)31-22-12-14-24-33(31)34)26-44-38(27-15-5-2-6-16-27,28-17-7-3-8-18-28)29-19-9-4-10-20-29/h2-24,34H,25-26H2,1H3,(H,39,42)(H,40,41)/t37-/m0/s1
• InChI Key: AWLPKAIRGNZKIN-QNGWXLTQSA-N
• Exact Mass: 599.21302971
• Molecular Formula: C38H33NO4S
• Molecular Weight: 599.7
• SMILES: C[C@](CSC(C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)(C(=O)O)NC(=O)OCC4C5=CC=CC=C5C6=CC=CC=C46
• Topological: 101
• Monoisotopic Mass: 599.21302971
• Synonyms: 725728-43-8, Fmoc-alpha-Me-L-Cys(Trt)-OH, N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-2-methyl-S-(triphenylmethyl)-L-cysteine, (R)-Fmoc-2-amino-2-methyl-3-tritylsulfanyl-propionic acid, Fmoc-alpha-Me-Cys(Trt)-OH, MFCD30749166, Fmoc-beta-Me-Cys(Trt)-OH, SCHEMBL3435366, Fmoc-S-trityl-alpha-Me-L-cysteine, N-Fmoc-2-methyl-S-trityl-L-cysteine, (R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-2-methyl-3-(tritylthio)propanoic acid, CS-0160399, D81095, (2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-2-methyl-3-tritylsulfanylpropanoic acid

Application

Fmoc-alpha-Me-L-Cys(Trt)-OH is primarily employed in peptide synthesis to introduce sterically constrained α-methyl-L-cysteine residues, which improve protease resistance and conformational rigidity in therapeutic peptides. It is essential for studying structure-activity relationships (SAR) in drug discovery and developing peptide-based inhibitors. The Trt-protected thiol group allows for selective deprotection and subsequent disulfide bond formation, critical for stabilizing peptide tertiary structures.

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