SYNTHESIS OF (2(R)UNDER-BAR,3(S)UNDER-BAR)[4-H-2(3)]VALINE - APPLICATION TO THE STUDY OF THE RING EXPANSION OF PENICILLIN-N BY DEACETOXYCEPHALOSPORIN-C SYNTHASE FROM STREPTOMYCES-CLAVULIGERUS

Authors
BALDWIN JE ADLINGTON RM CROUCH NP MELLOR LC MORGAN N SMITH AM SUTHERLAND JD
Citation
Je. Baldwin et al., SYNTHESIS OF (2(R)UNDER-BAR,3(S)UNDER-BAR)[4-H-2(3)]VALINE - APPLICATION TO THE STUDY OF THE RING EXPANSION OF PENICILLIN-N BY DEACETOXYCEPHALOSPORIN-C SYNTHASE FROM STREPTOMYCES-CLAVULIGERUS, Tetrahedron, 51(14), 1995, pp. 4089-4100
Citations number
25
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
51
Issue
14
Year of publication
1995
Pages
4089 - 4100
Database
ISI
SICI code
0040-4020(1995)51:14<4089:SO(-A>2.0.ZU;2-Z
Abstract
A new synthesis of (<2(R)under bar>,<3(S)under bar>)[4-H-2(3)] valine was developed, and used to synthesise (<2(R)under bar>) [2'-H-2(3)]-pe nicillin N via a chemico-enzymatic synthesis. This labelled penicillin was then used to demonstrate the stereospecific ring expansion of pen icillin N to deacetoxycephalosporin C by deacetoxycephalosporin C synt hase from Streptomyces clavuligerus.