BENARTHIN: A NEW INHIBITOR OF PYROGLUTAMYL PEPTIDASE III. SYNTHESIS AND STRUCTURE-ACTIVITY RELATIONSHIPS

MASAHIRO HATSU; MAKOTO TUDA; YASUHIKO MURAOKA; TAKAAKI AOYAGI; TOMIO TAKEUCHI

doi:10.7164/antibiotics.45.1088

The Journal of Antibiotics

Online ISSN : 1881-1469
Print ISSN : 0021-8820
ISSN-L : 0021-8820

BENARTHIN: A NEW INHIBITOR OF PYROGLUTAMYL PEPTIDASE

III. SYNTHESIS AND STRUCTURE-ACTIVITY RELATIONSHIPS

MASAHIRO HATSU, MAKOTO TUDA, YASUHIKO MURAOKA, TAKAAKI AOYAGI, TOMIO TAKEUCHI

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JOURNAL FREE ACCESS

1992 Volume 45 Issue 7 Pages 1088-1095

DOI https://doi.org/10.7164/antibiotics.45.1088

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Abstract

Benarthin, a new inhibitor of pyroglutamyl peptidase (PG-peptidase), has been isolated from the culture filtrate of Streptomyces xanthophaeus MJ244-SF1. The structure of benarthin has been determined to be L-(2, 3-dihydroxybenzoyl)arginyl-L-threonine. This structure was confirmed by the total synthesis of benarthin. Moreover, we synthesized benarthin derivatives to obtain information on the relationship between structure and inhibitory activity. The results indicated that the catechol group of benarthin is the essential moiety for the inhibition of PG-peptidase.

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