Specification
Description
Fmoc-Cys(STmp)-OH is a novel new tool for the regioselective synthesis of multiple disulfide bridged peptides by Fmoc SPPS. The STmp group is stable to piperidine but is extremely easy to remove by mild thiolysis. Albericio has reported removing four STmp groups on the solid phase with only three 5 minute treatments of 0.1 M N-methylmorpholine (NMM) in DMF containing 5% DTT.
Synonyms
Fmoc-Cys(STmp)-OH, N-α-Fmoc-S-2,4,6-trimethoxyphenylthio-L-cysteine
IUPAC Name
(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[(2,4,6-trimethoxyphenyl)disulfanyl]propanoic acid
Canonical SMILES
COC1=CC(=C(C(=C1)OC)SSCC(C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24)OC
InChI
1S/C27H27NO7S2/c1-32-16-12-23(33-2)25(24(13-16)34-3)37-36-15-22(26(29)30)28-27(31)35-14-21-19-10-6-4-8-17(19)18-9-5-7-11-20(18)21/h4-13,21-22H,14-15H2,1-3H3,(H,28,31)(H,29,30)/t22-/m0/s1
InChI Key
GADCBXMSWHDNAU-QFIPXVFZSA-N
Boiling Point
742.3±60.0 ℃at 760 mmHg
Application
Peptide synthesis.
Reaction Suitability
reaction type: Fmoc solid-phase peptide synthesis
Storage Temperature
15-25℃
Vapor Pressure
0.0±2.6 mmHg at 25℃