Open AccessA CD Exciton Chirality Method for Determination of the Absolute Configuration of threo-β-Aryl-β-hydroxy-α-amino Acid Derivatives
Author(s) -
LeeChiang Lo,
ChunTzu Yang,
CharngSheng Tsai
Publication year - 2002
Publication title -
the journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.2
H-Index - 228
eISSN - 1520-6904
pISSN - 0022-3263
DOI - 10.1021/jo016070l
Subject(s) - chemistry , chirality (physics) , absolute configuration , aryl , stereochemistry , amino acid , chromophore , serine , conformational isomerism , beta (programming language) , threonine , coupling constant , molecule , organic chemistry , chiral symmetry , physics , biochemistry , alkyl , quantum mechanics , computer science , nambu–jona lasinio model , programming language , enzyme , quark , particle physics
The absolute configuration of threo-beta-aryl-beta-hydroxy-alpha-amino acids was studied by CD exciton chirality method using 7-diethylaminocoumarin-3-carboxylate as a red-shifted chromophore. Bischromophoric derivatives for a series of threo-beta-aryl-beta-hydroxy-alpha-amino acids (3a-h) were prepared and their CD spectra measured in CH2Cl2. By combining the data of CD and NMR coupling constants, we are able to correlate their preferred conformer (B) and the positive CD to the corresponding (2S,3R)-absolute configuration. These results are consistent with those obtained from serine and threonine derivatives, which represent the simplest form of beta-hydroxy-alpha-amino acids. This CD method could thus become a general method for determining the absolute configuration of threo-beta-aryl-beta-hydroxy-alpha-amino acids.
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