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Synthesis, Structure and Configuration of Streptanoate
Author(s) -
Li MeiMei,
Xu ZeJun,
Wu Yikang,
Liu Bo
Publication year - 2018
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201702871
Subject(s) - diastereomer , absolute configuration , optical rotation , sample (material) , rotation (mathematics) , chemistry , spectral line , crystallography , stereochemistry , nuclear magnetic resonance , physics , computer science , organic chemistry , artificial intelligence , chromatography , astronomy
Diastereomers (of different relative configurations) of the reported gross structure and all its possible alternatives were synthesized. However, none of them showed NMR and optical rotation consistent with those in the literature. The very confusing data discrepancies and the unavoidable doubt about the identity of the natural sample caused by the deficiencies (e. g. inadequate sample purity, unsatisfactory quality of NMR spectra and human errors) hidden in the previous work were eventually resolved through reveal of a so far unnoticed effect of CDCl 3 on the NMR of streptanoate in DMSO‐ d 6 . The new systematic spectral data show that streptanoate should have a hydroxybutanoylamino acid gross structure with a (2 R ,2’ R ) absolute configuration.