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Fmoc-D-Ser(Msbh)-OH
Chemical name: N-(((9H-fluoren-9-yl)methoxy)carbonyl)-O-(bis(4-(methylsulfinyl)phenyl)methyl)-D-serine // Synonyms: Safety-Catch D-Serine
- Product code:FAA8837
- Formula:C33H31NO7S2
- Molecular weight:617.73 g/mol
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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
The p-(methylsulfinyl)benzyl group: a trifluoroacetic acid (TFA)-stable carboxyl-protecting group readily convertible to a TFA-labile group; J. M. Samanen, E. Brandeis; J. Org. Chem. 1988; 53(3): 561-569. https://doi.org/10.1021/jo00238a016
Solid-Phase Synthesis Using a Four-Dimensional (Safety-Catch) Protecting Group Scheme; F. Albericio, S. Noki, E. Brasil, H. Zhang, T. Bruckdorfer, B. G. de la Torre; J. Org. Chem. 2022; 87: 9443-9453. https://doi.org/10.1021/acs.joc.2c01056
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