STUDIES ON THE STEREOSPECIFICITY OF THE CLAVAMINIC ACID SYNTHASE CATALYZED HYDROXYLATION REACTION

被引：23

作者：

BALDWIN, JE

MERRITT, KD

SCHOFIELD, CJ

ELSON, SW

BAGGALEY, KH

机构：

[1] SMITHKLINE BEECHAM PHARMACEUT,BETCHWORTH RH3 7AJ,SURREY,ENGLAND

[2] OXFORD CTR MOLEC SCI,OXFORD OX1 3QY,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1993年 / 16期

关键词：

D O I：

10.1039/c39930001301

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Incubation of (2S,3S)-5-guanidino[2,3-H-2(2)]-2-(2'-oxoazetidin-1'-yl)pentanoic acid and (2S,3R)-5-guanidino-[3-H-2(1)]-2-(2'-oxoazetidin-1'-yl)pentanoic acid with clavaminic acid synthase resulted in highly stereospecific hydroxylation at C-3, with removal of the pro-R hydrogen or deuterium, respectively.

引用

页码：1301 / 1302

页数：2

共 21 条

[1] SYNTHESIS OF THE NOVEL MONOCYCLIC BETA-LACTAM PROCLAVAMINIC ACID
BAGGALEY, KH
SIME, JT
NICHOLSON, NH
ELSON, SW
GILLETT, J
HOLLAND, S
WORONIECKI, SR
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (22) : 1738 - 1739
[2] STUDIES ON THE BIOSYNTHESIS OF CLAVULANIC ACID .5. ABSOLUTE STEREOCHEMISTRY OF PROCLAVAMINIC ACID, THE MONOCYCLIC BIOSYNTHETIC PRECURSOR OF CLAVULANIC ACID
BAGGALEY, KH
ELSON, SW
NICHOLSON, NH
SIME, JT
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (06): : 1521 - 1533
[3] SYNTHESIS OF L-ORNITHINES STEREOSPECIFICALLY DEUTERATED AT C-3
BALDWIN, JE
MERRITT, KD
SCHOFIELD, CJ
[J]. TETRAHEDRON LETTERS, 1993, 34 (24) : 3919 - 3920
[4] ISOLATION OF DIHYDROCLAVAMINIC ACID, AN INTERMEDIATE IN THE BIOSYNTHESIS OF CLAVULANIC ACID
BALDWIN, JE
ADLINGTON, RM
BRYANS, JS
BRINGHEN, AO
COATES, JB
CROUCH, NP
LLOYD, MD
SCHOFIELD, CJ
ELSON, SW
BAGGALEY, KH
CASSELS, R
NICHOLSON, N
[J]. TETRAHEDRON, 1991, 47 (24) : 4089 - 4100
[5] ISOLATION OF AN INTERMEDIATE IN CLAVULANIC ACID BIOSYNTHESIS
BALDWIN, JE
ADLINGTON, RM
BRYANS, JS
BRINGHEN, AO
COATES, JB
CROUCH, NP
LLOYD, MD
SCHOFIELD, CJ
ELSON, SW
BAGGALEY, KH
CASSELLS, R
NICHOLSON, N
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (08) : 617 - 619
[6] A SUBSTRATE-ANALOG STUDY ON CLAVAMINIC ACID SYNTHASE - POSSIBLE CLUES TO THE BIOSYNTHETIC ORIGIN OF PROCLAVAMIC ACID
BALDWIN, JE
LLOYD, MD
WHASON, B
SCHOFIELD, CJ
ELSON, SW
BAGGALEY, KH
NICHOLSON, NH
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (06) : 500 - 502
[7] BALDWIN JE, UNPUB
[8] STEREOCHEMICAL COURSE OF THE KEY RING-FORMING REACTIONS IN CLAVULANIC ACID BIOSYNTHESIS
BASAK, A
SALOWE, SP
TOWNSEND, CA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (04) : 1654 - 1656
[9] 1H-PYRAZOLE-1-CARBOXAMIDINE HYDROCHLORIDE - AN ATTRACTIVE REAGENT FOR GUANYLATION OF AMINES AND ITS APPLICATION TO PEPTIDE-SYNTHESIS
BERNATOWICZ, MS
WU, YL
MATSUEDA, GR
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (08) : 2497 - 2502
[10] NATURALLY-OCCURRING BETA-LACTAMASE INHIBITORS WITH ANTIBACTERIAL ACTIVITY
BROWN, AG
BUTTERWORTH, D
COLE, M
HANSCOMB, G
HOOD, JD
READING, C
[J]. JOURNAL OF ANTIBIOTICS, 1976, 29 (06) : 668 - 669

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