Angiotensin converting enzyme inhibitory activity of amino acid esters of carbohydrates

International Journal of Biological Macromolecules
Vasudeva KamathSoundar Divakar

Abstract

L-alanyl-D-glucose, L-valyl-D-glucose, L-phenylalanyl-D-glucose and L-phenylalanyl-lactose esters were synthesized enzymatically using two lipases viz., Rhizomucor miehei lipase (RML) and porcine pancreas lipase (PPL) and tested for their potential as inhibitors of angiotensin converting enzyme (ACE) in vitro. The esters exhibited concentration related ACE inhibitory activity. The potency of the various esters measured in terms of IC50 values were as follows: L-phenylalanyl-D-glucose, IC50-0.121 mM (mixture of five diastereomeric esters: 6-O-24.1%; 3-O-23.3%; 2-O-19.2%; 2,6-di-O-16.6% and 3,6-di-O-16.8% from the total yield of 92.4%); L-phenylalanyl-lactose, IC50-0.229 mM (mixture of three diastereomeric esters: 6-O-42.1%; 6'-O-30.9%; and 6,6'-di-O-27.0% from the total yield of 50.58%); alanyl-D-glucose, IC50-0.23 mM (mixture of five diastereomeric esters: 6-O-46.7%; 3-O-11.5%; 2-O-19.9%; 2,6-di-O-6.6% and 3,6-di-O-15.3% from the total yield of 26.5%) and L-valyl-D-glucose, IC50-0.396 mM (mixture of five diastereomeric esters: 6-O-32.4%; 3-O-26.5%; 2-O-26.4%; 2,6-di-O-8.8% and 3,6-di-O-5.9% from the total yield of 68.2%). These in vitro data suggest a potential therapeutic role for the aminoesters of carbohydrates as inhibibito...Continue Reading

References

Jul 1, 1986·Chemical & Pharmaceutical Bulletin·A MorigiwaN Ikekawa
Jul 1, 1971·Biochemical Pharmacology·D W Cushman, H S Cheung
Jan 1, 1995·Plant Foods for Human Nutrition·A OkamotoF Yanagida
Dec 13, 2000·Journal of Molecular Recognition : JMR·O A KostT A Orth
Sep 6, 2002·Bioorganic & Medicinal Chemistry·Manju BalaSantosh Pasha
Apr 5, 2003·The International Journal of Biochemistry & Cell Biology·David Coates
Feb 18, 2004·Current Drug Metabolism·Tomohiro Terada, Ken-ichi Inui
Apr 16, 2005·Journal of Biotechnology·Kenchaiah Lohith, Soundar Divakar
May 3, 2005·Bioorganic & Medicinal Chemistry·Ronghua HuangSe-Kwon Kim

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Citations

Jun 7, 2017·Critical Reviews in Biotechnology·Jakub StarońMaciej Guzik

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