ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The title compound was prepared via a malonic ester synthesis starting with α-chloromethylpyrazine [2], and ending, after an asymmetric enzymatic hydrolysis of the racemic N-acetyl-β-2-pyrazinylalanine to the L-form of the new amino acid. The optical purity was ascertained by 1H-NMR analysis at 360 MHz of the diastereoisomeric dipeptides L-pyrazinylalanine-L-leucine and D-pyrazinylalanine-L-leucine. Hydrophobic, steric and electronic parameters for its side chain were also estimated, which can be useful for the quantitative study of structure-activity relationships of biologically active peptide derivatives. The new amino acid could be introduced in the place of phenylalanine in the enkephalin-like pentapeptide [D-alanyl2, leucine5]enkephalin, thus showing good stability towards the classical methods of peptide synthesis.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19830660518
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