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CD exciton chirality method for determination of the absolute configuration of β‐hydroxy‐α‐amino acid derivatives
Author(s) -
Lo LeeChiang,
Chen JeanYin,
Yang ChunTzu,
Gu DerShang
Publication year - 2001
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.1029
Subject(s) - chemistry , chirality (physics) , absolute configuration , chromophore , carboxylate , conformational isomerism , stereochemistry , serine , amino acid , threonine , exciton , coupling constant , polar , molecule , photochemistry , organic chemistry , chiral symmetry , biochemistry , physics , quantum mechanics , particle physics , astronomy , nambu–jona lasinio model , enzyme , quark
The absolute configuration of β‐hydroxy‐α‐amino acids was studied by CD exciton chirality method using 7‐diethylaminocoumarin‐3‐carboxylate as a red‐shifted chromophore. The CD spectra of bischromophoric derivatives of ( S )‐serine and (2 S ,3 R )‐threonine methyl esters ( 2 and 7 ) were compared with those of acyclic vic ‐aminoalcohols and diols ( 3–6 and 8–9 ). This study indicates that the polar carboxylate group of β‐hydroxy‐α‐amino acids makes them a unique subclass of vic ‐aminoalcohols. By combining the data of CD and NMR coupling constants, we are able to correlate their preferred conformer B and positive CD to the corresponding absolute configuration. Chirality 13:266–271, 2001. © 2001 Wiley‐Liss, Inc.