Specification
Description
Building block for introduction of N-α-methyl-cysteine amino-acid residues by Fmoc SPPS. Fmoc SPPS of Cysteine-Containing Peptides
Synonyms
N-α-Fmoc-N-α-methyl-S-trityl-L-cysteine
InChI
1S/C38H33NO4S/c1-39(37(42)43-25-34-32-23-13-11-21-30(32)31-22-12-14-24-33(31)34)35(36(40)41)26-44-38(27-15-5-2-6-16-27,28-17-7-3-8-18-28)29-19-9-4-10-20-29/h2-24,34-35H,25-26H2,1H3,(H,40,41)/t35-/m0/s1
InChI Key
RAKOPMQMPUNRGI-DHUJRADRSA-N
Application
Fmoc-N-Me-Cys(Trt)-OH is a Fmoc-protected derivative of N-methyl cysteine used as a building block to prepare peptide thioesters under acidic conditions. The residue attached to the amino group of N-methylcysteine can migrate to the cysteinyl thiol group, resulting in the formation of a peptide thioester. The introduction of this Fmoc-protected derivative is best achieved using HATU as a coupling reagent in the presence of DIPEA (N, N-Diisopropylethylamine).
It can also be used to prepare Fmoc-N-Me-Cys(Trt)-OAllyl intermediate for the solid-phase synthesis of dithiol Triostin A.
Optical Activity
[α]22/D -25.0°, c = 0.5% in dichloromethane
Reaction Suitability
reaction type: Fmoc solid-phase peptide synthesis