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Fmoc-D-Cys(Msbh)-OH
Chemical name: N-alpha-(9-Fluorenylmethyloxycarbonyl)-S-(4,4'-dimethylsulfinylbenzhydryl)-D-cysteine // Synonyms: Fmoc-D-Cys(MSBH), (2S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(bis(4-(methylsulfinyl)phenyl)methylthio)propanoic acid, Safety-Catch D-Cysteine
- Product code:FAA8150
- Formula:C33H31NO6S3
- Storage temperature:2-8°C
- Molecular weight:633.80 g/mol
from $1,250.00
description
MsbH is a safety-catch protecting group for cysteines, serines and threonines. It is stable to the conditions applied in both Boc and Fmoc chemistry. By reduction of the sulfoxides to thioethers with NH4I and dimethylsulfide in TFA, the MsbH protection becomes instable and is instantly removed.
references
Total Synthesis of Human Hepcidin through Regioselective Disulfide-Bond Formation by using the Safety-Catch Cysteine Protecting Group 4,4'-Dimethylsulfinylbenzhydryl; Zoltan Dekan, Mehdi Mobli, Michael W. Pennington, Eileen Fung, Elizabeta Nemeth, and Paul F. Alewood; Angew. Chem. Int. Ed. 2014; 53: 2931-2934. DOI: 10.1002/anie.201310103.
A new safety-catch protecting group and linker for solid-phase synthesis. Sathiah Thennarasu, Chuan-Fa Liu; Tetrahedron Lett. 2010; 51(24): 3218-3220. DOI: 10.1016/j.tetlet.2010.04.047
A Reductive Acidolysis Final Deprotection Strategy in Solid Phase Peptide Synthesis Based on Safety-Catch Protection. Tooru Kimura, Toshio Fukui, Shigeki Tanaka, Kenichi Akaji, Yoshiaki Kiso; Chem. Pharm. Bull. 1997; 45: 18-26. DOI: 10.1248/cpb.45.18
Safety-catch anchoring linkage for synthesis of peptide amides by Boc/Fmoc strategy. Marcel Pátek, Michal Lebl; Tetrahedron Lett. 1991; 32(31): 3891-3894. DOI: 10.1016/S0040-4039(00)79406-8
The p-(methylsulfinyl)benzyl group: a trifluoroacetic acid (TFA)-stable carboxyl-protecting group readily convertible to a TFA-labile group. James M. Samanen, Ester Brandeis; J. Org. Chem. 1988; 53(3): 561-569. DOI: 10.1021/jo00238a016
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