PROPIOXATINS A AND B, NEW ENKEPHALINASE B INHIBITORS: III. TOTAL SYNTHESIS OF PROPIOXATIN A

Propioxatin A, a potent enkephalinase B inhibitor produced by Kitasatosporia setae SANK 60684, was synthesized. The synthetic route involved a regio-selective synthesis of O-benzyl-α-propylsuccinic acid monohydroxamic acid via the acid chloride of α-propylsuccinic acid. The stereoisomer of the N-acy...

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Bibliographic Details
Published in:Journal of antibiotics 1986, Vol.39(10), pp.1382-1385
Main Authors: INAOKA, YOSHINORI, TAKAHASHI, SHUJI, SATO, SADAO
Format: Article
Language:English
Subjects:
Aminoacids and peptides
Chemical Phenomena
Chemistry
Condensed matter: structure, mechanical and thermal properties
Dipeptides - chemical synthesis
Exact sciences and technology
Organic chemistry
Organic compounds
Peptides
Physics
Preparations and properties
Protease Inhibitors - chemical synthesis
Structure of solids and liquids
crystallography
Structure of specific crystalline solids
X-Ray Diffraction
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Summary:Propioxatin A, a potent enkephalinase B inhibitor produced by Kitasatosporia setae SANK 60684, was synthesized. The synthetic route involved a regio-selective synthesis of O-benzyl-α-propylsuccinic acid monohydroxamic acid via the acid chloride of α-propylsuccinic acid. The stereoisomer of the N-acyl moiety of natural propioxatin A was analyzed by X-ray crystallography in the form of the di-O-benzyl ester and was determined as S. Devalyl propioxatin A synthesized by the same method showed a higher Ki value for enkephalinase B than propioxatin A.
ISSN:0021-8820
1881-1469
DOI:10.7164/antibiotics.39.1382