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A method for determining absolute configuratiom of β-amino acids by CD spectra of their DNP derivatives

✍ Scribed by Ukon Nagai; Masao Kawai; Takashi Yamada; Shigeru Kuwata; Hiroshi Watanabe

Publisher
Elsevier Science
Year
1981
Tongue
French
Weight
147 KB
Volume
22
Category
Article
ISSN
0040-4039

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✦ Synopsis

Aromatic B-amino acids were converted to the Dnp derivatives, and aliphatic ones to Dnp-pMA derivatives.

The sign of the Cotton effect near 400 nm reflected the configuration at the B-position without exception.

Thus, the relation seems to afford a new reliable method for determining the absolute configuration of B-amino acids. 4_Dinitrophenyl(Dnp) derivatives of aromatic a-amino acids exhibit characteristic CD spectra above 300 nm. The sign of the band near 400 nm has high degree of correlation to the absolute configuration at the a-carbon atom (Dnp-aromatic rule).

  1. The characteristic CD pattern is considered to be caused by interaction of the Dnp-and the aromatic chromophores. CD spectra of similar pattern but of opposite sign were observed for p-methoxyanilides(pMA) of aliphatic Dnp-u-amino acids with the same configuration.

  2. In this paper, extension of the two rules to B-amino acids is described.

Some antibiotic peptides, such as bottromycin, bleomycin, iturin A, blasticidin S, and so on, contain $-amino acids as their components.

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