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The Synthesis and Characterization of a Pentafluorosulfanylated Peptide
Author(s) -
Lim Dong Sung,
Lin JinHong,
Welch John T.
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201200327
Subject(s) - chemistry , peptide , diastereomer , amino acid , stereochemistry , sequence (biology) , heptad repeat , characterization (materials science) , peptide sequence , biochemistry , nanotechnology , materials science , gene
Abstract The design and synthesis of pentafluorosulfanyl‐containing heptad amino acid sequence was described. The three‐dimensional conformation of the peptide was investigated by using CYANA (combined assignment and dynamics algorithm for NMR applications) and the integrated autoassignment. This study shows that the one of the diastereomers assumed a very tight coiled conformation in [D 6 ]DMSO where both pentafluorosulfanyl groups assumed a synclinal relationship. The propensity of the protected heptapeptide to form such a tight coil and of the pentafluorosulfanyl groups to align so uniformly is suggestive of the utility of pentafluorosulfanylated amino acids in promoting conformational control.