Lactam ring stability of stereoisomers of 4-amino-substituted pyroglutamic acids in acidic medium / Vigorov A. Yu.,Nizova I. A.,Tumashov A. A.,Ezhikova M. A.,Kodess M. I.,Krasnov V. P. // RUSSIAN CHEMICAL BULLETIN. - 2014. - V. 63, l. 6. - P. 1317-1321.

ISSN/EISSN:

1066-5285 / 1573-9171

Type:

Article

Abstract:

The acid hydrolysis of the lactam ring of cis and trans stereoisomers of 4-(1-piperidy1)-, 4-dibenzylamino-, 4- {[}(methyl)(phenyl)amino] 4-phenylamino-, and 4-(4-methoxypheny1)aminopyroglutamic acids was studied. It was shown that the relative stability of the lactam ring of 4-amino-substituted pyroglutamic acids to acid hydrolysis depends both on the structure of a substituent in the position 4 and on the configuration of the compounds studied. Among these compounds, 4-amino- 1-arylpyroglutamic acids were the most stable in acidic medium. The trans isomers are more stable than the corresponding cis isomers.

Author keywords:

glutamic acid; high performance liquid chromatography; hydrolysis; lactam; pyroglutamic acid; NMR GAMMA-HYDROXYGLUTAMIC ACID; CIS-PEPTIDE-BOND; GLUTAMIC-ACID; ASYMMETRIC-SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; 4-AMINO DERIVATIVES; ANALOGS; MECHANISM; KINETICS; 5-OXOPROLINE

DOI:

нет данных

Web of Science ID:

ISI:000350877500009

Соавторы в МНС:

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Другие поля

Поле	Значение
Month	JUN
Publisher	SPRINGER
Address	233 SPRING ST, NEW YORK, NY 10013 USA
Language	English
EISSN	1573-9171
Keywords-Plus	GAMMA-HYDROXYGLUTAMIC ACID; CIS-PEPTIDE-BOND; GLUTAMIC-ACID; ASYMMETRIC-SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; 4-AMINO DERIVATIVES; ANALOGS; MECHANISM; KINETICS; 5-OXOPROLINE
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Multidisciplinary
Author-Email	vigorov@ios.uran.ru
Funding-Acknowledgement	Russian Foundation for Basic Research {[}14-03-31357, 13-03-12188]; Ural Branch of the Russian Academy of Sciences {[}12-P-3-1030]; Council on Grants at the President of the Russian Federation {[}NSh-3656.2014.3]
Funding-Text	This work was financially supported by the Russian Foundation for Basic Research (Project Nos 14-03-31357 and 13-03-12188), the Ural Branch of the Russian Academy of Sciences (Project 12-P-3-1030), and the Council on Grants at the President of the Russian Federation (Program of State Support for Leading Scientific Schools of the Russian Federation, Grant NSh-3656.2014.3).
Number-of-Cited-References	52
Usage-Count-Since-2013	2
Journal-ISO	Russ. Chem. Bull.
Doc-Delivery-Number	CD2BC