J. Baldwin, R. Adlington, M. F. Parisi
1986
Citations
0
Influential Citations
18
Citations
Journal
Tetrahedron
Abstract
Abstract The unusual cyclobutanol containing dipeptide (1 S ,2 S )-1-Hydroxy-2-[(S)-valylamino]cyclobutane-1-acetic acid (1), produced by an as yet unidentified Streptomyces species X-1092, has been synthesised via a short stereoselective route. Acid hydrolysis of (1) gave (1 S ,2 S )-1-hydroxy-2-aminocyclobutane-1-acetic acid (2) which in direct comparison tests to (1) gave enhanced antibacterial activity against the gram-positive organism Bacillus subtilis A.T.C.C. 6633. An intriguing mechanism in which (2) acts as a “suicide substrate” for the crucial pyridoxal based enzyme cystathionine-γ-synthetase thus creating the antibacterial effect is proposed; a biomimetic study supports this proposal.