Chemo-enzymatic synthesis of bicyclic gamma-lactams using clavaminic acid synthase

Incubation of the γ-lactam analogue of proclavaminic acid, (±)-threo-5-amino-3-hydroxy-2-(1'-aza-2'-oxocyclopentyl) acid, led to production of two bicyclic γ-lactam products.

Bibliografiske detaljer
Main Authors:	Baldwin, J, Adlington, R, Bryans, J, Lloyd, MD, Sewell, T, Schofield, C, Baggaley, K, Cassels, R
Format:	Journal article
Udgivet:	1997

Lignende værker

ENZYMATIC-SYNTHESIS OF BICYCLIC GAMMA-LACTAMS USING CLAVAMINIC ACID SYNTHASE
af: Baldwin, J, et al.
Udgivet: (1992)

SUBSTRATE-ANALOG STUDIES ON CLAVAMINIC ACID SYNTHASE
af: Baldwin, J, et al.
Udgivet: (1993)

FORMATION OF A NOVEL BICYCLIC GAMMA-LACTAM WITH ISOPENICILLIN-N SYNTHASE
af: Baldwin, J, et al.
Udgivet: (1989)

STUDIES ON THE STEREOSPECIFICITY OF THE CLAVAMINIC ACID SYNTHASE CATALYZED HYDROXYLATION REACTION
af: Baldwin, J, et al.
Udgivet: (1993)

Product-substrate engineering by bacteria: Studies on clavaminate synthase, a trifunctional dioxygenase
af: Lloyd, MD, et al.
Udgivet: (1999)

GAMMA-LACTAM FORMATION FROM TRIPEPTIDES WITH ISOPENICILLIN-N SYNTHASE
af: Baldwin, J, et al.
Udgivet: (1988)

A SUBSTRATE-ANALOG STUDY ON CLAVAMINIC ACID SYNTHASE - POSSIBLE CLUES TO THE BIOSYNTHETIC ORIGIN OF PROCLAVAMIC ACID
af: Baldwin, J, et al.
Udgivet: (1993)

EXPRESSION IN ESCHERICHIA-COLI OF A CLAVAMINIC ACID SYNTHASE ISOZYME - A TRIFUNCTIONAL OXYGENASE INVOLVED IN CLAVULANIC ACID BIOSYNTHESIS
af: Lawlor, E, et al.
Udgivet: (1994)

SYNTHESIS OF A BICYCLIC GAMMA-LACTAM DIPEPTIDE ANALOG
af: Baldwin, J, et al.
Udgivet: (1992)

SYNTHESIS OF A NOVEL BICYCLIC GAMMA-LACTAM ANALOG OF THE 1-OXAPENAMS
af: Baldwin, J, et al.
Udgivet: (1989)

SYNTHESIS OF A BICYCLIC GAMMA-LACTAM DIPEPTIDE ANALOG
af: Baldwin, J, et al.
Udgivet: (1993)

Structural origins of the selectivity of the trifunctional oxygenase clavaminic acid synthase.
af: Zhang, Z, et al.
Udgivet: (2000)

GAMMA-LACTAM ANALOGS OF CARBAPENICILLANIC ACIDS
af: Baldwin, J, et al.
Udgivet: (1985)

GAMMA-LACTAM ANALOGS OF CARBAPENICILLANIC ACIDS
af: Baldwin, J, et al.
Udgivet: (1986)

Mutagenesis studies on the iron binding ligands of clavaminic acid synthase.
af: Doan, L, et al.
Udgivet: (2000)

X-ray absorption spectroscopic studies of the iron(II) active site of clavaminic acid synthase.
af: Baldwin, J, et al.
Udgivet: (1997)

Mechanism for cyclization reaction by clavaminic acid synthase. Insights from modeling studies.
af: Borowski, T, et al.
Udgivet: (2007)

γ-Lactam analogues of carbapenicillanic acids
af: Baldwin, J, et al.
Udgivet: (1986)

A GAMMA-LACTAM ANALOG OF THE PENEMS POSSESSING ANTIBACTERIAL ACTIVITY
af: Baldwin, J, et al.
Udgivet: (1989)

On the diastereoselectivity of alkylations of bicyclic lactams
af: Bailey, J, et al.
Udgivet: (2000)

ISOLATION OF DIHYDROCLAVAMINIC ACID, AN INTERMEDIATE IN THE BIOSYNTHESIS OF CLAVULANIC ACID
af: Baldwin, J, et al.
Udgivet: (1991)

THE SYNTHESIS OF POTENTIAL GAMMA-LACTAM ANTIBIOTICS CONTAINING A CYCLOSERINE NUCLEUS
af: Baldwin, J, et al.
Udgivet: (1990)

A GAMMA-LACTAM ANALOG OF PENEMS POSSESSING ANTIBACTERIAL ACTIVITY
af: Baldwin, J, et al.
Udgivet: (1986)

Crystal structure of a clavaminate synthase-Fe(II)-2-oxoglutarate-substrate-NO complex: evidence for metal centered rearrangements.
af: Zhang, Z, et al.
Udgivet: (2002)

Stereoselective oxygenation of bicyclic lactams
af: Cottrell, I, et al.
Udgivet: (2004)

Enzymatic synthesis of monocyclic beta-lactams.
af: Sleeman, M, et al.
Udgivet: (2002)

Reversible acylation of elastase by gamma-lactam analogues of beta-lactam inhibitors
af: Westwood, N, et al.
Udgivet: (1997)

Biocatalytic production of bicyclic β-lactams with three contiguous chiral centres using engineered crotonases
af: Hamed, R, et al.
Udgivet: (2019)

Synthesis and Antibacterial Activity of Bicyclic Lactam-Lactones
af: Angelov, P, et al.
Udgivet: (2011)

Roles of 2-oxoglutarate oxygenases and isopenicillin N synthase in ß-lactam biosynthesis
af: Rabe, P, et al.
Udgivet: (2018)

Synthesis of a bicyclic oxo-γ-lactam from a simple caprolactam derivative
af: Weck, C, et al.
Udgivet: (2017)

Enantiopure bicyclic piperidinones: stereoselectivity in lactam enolate alkylations.
af: Brewster, A, et al.
Udgivet: (2004)

Studies of isopenicillin N synthase enzymatic properties using a continuous spectrophotometric assay.
af: Dubus, A, et al.
Udgivet: (2000)

THE ENZYMATIC CONVERSION OF EXOMETHYLENE CEPHALOSPORIN-C INTO DEACETYL CEPHALOSPORIN-C AND THE ROLE OF MOLECULAR-OXYGEN IN CEPHALOSPORIN-C BIOSYNTHESIS
af: Baldwin, J, et al.
Udgivet: (1988)

AN EFFECTIVE SUBSTITUTE FOR ALPHA-AMINOADIPIC ACID IN THE ENZYMATIC-SYNTHESIS OF PENICILLINS
af: Baldwin, J, et al.
Udgivet: (1987)

ISOLATION OF AN INTERMEDIATE IN CLAVULANIC ACID BIOSYNTHESIS
af: Baldwin, J, et al.
Udgivet: (1990)

CEPHALOSPORIN-C BIOSYNTHESIS - STEREOCHEMISTRY OF THE INCORPORATION OF D,L,D-ALPHA-AMINODIPOYL-CYSTEINYL-(3S)-[2-2H,4-C-13]VALINE INTO BETA-LACTAM COMPOUNDS
af: Baldwin, J, et al.
Udgivet: (1989)

Uncatalysed diaryldiazo cyclopropanations on bicyclic lactams: access to annulated prolines.
af: Harris, L, et al.
Udgivet: (2015)

Bicyclic lactams derived from serine or cysteine and 2-methylpropanal
af: Bagum, H, et al.
Udgivet: (2020)

STEPWISE HYDROGEN REMOVAL IN THE ENZYMATIC RING EXPANSION OF PENICILLIN-N TO DEACETOXYCEPHALOSPORIN-C
af: Baldwin, J, et al.
Udgivet: (1987)