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Fmoc-L-Cys(Thp)-OH
Chemical name: N-alpha-(9-Fluorenylmethyloxycarbonyl)-S-tetrahydropyranyl-L-cysteine // Synonyms: Fmoc-Cys(Thp)-OH, (R)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(tetrahydro-2H-pyran-2-ylthio)propanoic acid
- Product code:FAA4160
- CAS No.:1673576-83-4
- Formula:C23H25NO5S
- Storage temperature:-20°C
- Molecular weight:427.15 g/mol
from $437.50
description
Tetrahydropyranyl (Thp), a new S,O-acetal nonaromatic protecting group for cysteine, which has been shown to be superior to Trt, Dpm, Acm, and StBu in solid-phase peptide synthesis using the Fmoc/tBu strategy. Cys racemization and C-terminal 3-(1-piperidinyl)-alanine formation were minimized when the Cys was protected with Thp accompanied by improved solubility of Cys-containing protected peptides. Complete deprotection can be carried out with either TFA/TIS/DCM (10:1.5:88.5) within 5 min or with HCl/dioxane (12:88)in 2h.
references
Tetrahydropyranyl, a Nonaromatic Acid-Labile Cys Protecting Group for Fmoc Peptide Chemistry; I. Ramos-Tomillero, H. Rodriguez and F. Albericio; Organic Letters 2015; 17: 1680-1683. doi:10.1021/acs.orglett.5b00444
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