CD exciton chirality method for determination of the absolute configuration of β-hydroxy-α-amino acid derivatives

✍ Scribed by Lee-Chiang Lo; Jean-Yin Chen; Chun-Tzu Yang; Der-Shang Gu

• Publisher: John Wiley and Sons
• Year: 2001
• Tongue: English
• Weight: 195 KB
• Volume: 13
• Category: Article
• ISSN: 0899-0042
• DOI: 10.1002/chir.1029

✦ Synopsis

The absolute configuration of beta-hydroxy-alpha-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 (2S,3R)-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 beta-hydroxy-alpha-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.