Chemical interconversion of the .beta.-lactam antibiotics

Cooper, R. D. G.; Hatfield, Lowell D.; Spry, Douglas O.

doi:10.1021/ar50061a005

Cited by 47 publications

(11 citation statements)

References 18 publications

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“…However, the most economical route to this class of compounds involves the acid-catalyzed rearrangement of penicillin sulfoxides (161,162). Since the disclosure of this rearrangement in 1963, a tremendous number of papers dealing with the nature of the catalyst, solvent, optimal reaction parameters, and the reaction mechanism have appeared and been thoroughly reviewed (87,(163)(164)(165). In addition, over twenty U.S. patents dealing with this process have been issued (87).…”

Section: -Methyl Cephalosporinsmentioning

confidence: 99%

Cephalosporins

Roberts¹

2000

Kirk-Othmer Encyclopedia of Chemical Technology

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CEPHALOSPORINSThe cephalosporins, a subgroup of β-lactam antibiotics, consist of a 4-membered lactam ring fused through the nitrogen and the adjacent tetrahedral carbon atom to a second heterocycle forming a 6-membered dihydrothiazine ring. Other structural features common to all the cephalosporins are a carboxyl group on the dihydrothiazine ring on the carbon next to the ring nitrogen and a functionalized amino group on C-7, the carbon of the β-lactam ring opposite the nitrogen. These features are evidenced in 7-aminocephalosporanic acid [957-68-6] (7-ACA), C 10 H 12 N 2 O 5 S 1. Cephalosporins, like all β-lactam antibiotics, exert their antibacterial effect by interfering with the synthesis of the bacterial cell wall. These antibiotics tend to be "irreversible" inhibitors of cell wall biosynthesis and they are usually bactericidal at concentrations close to their bacteriostatic levels. Cephalosporins are widely used for treating bacterial infections. They are highly effective antibiotics and have low toxicity.

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Section: -Methyl Cephalosporinsmentioning

confidence: 99%

Cephalosporins

Roberts¹

2000

Kirk-Othmer Encyclopedia of Chemical Technology

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“…12) (Morin et at., 1963). This unique type of reaction, the details of which are beyond the scope of this review, has now been extensively investigated (Cooper and Spry, 1972;Cooper and Koppel, 1982) and shown H H j.- to proceed through an alkene-sulfenic acid intermediate (Cooper et at., 1973). The application of this chemistry for the preparation of semisynthetic deacetoxycephalosporins from the readily available penicillins was soon to be recognized.…”

Section: Chemical Interrelationsmp Between Penicillins and Cephalospomentioning

confidence: 99%

Penicillium and Acremonium

Peberdy¹

1987

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v Foreword Biotechnology is a word that was originally coined to describe the new processes which could be derived from our ability to manipulate, in vitro, the genetic material common to all organisms. I t has now become a generic term encompassing all "applications" of living systems, including the more traditional fermentation and agricultural industries. Recombinant DNA technology has opened up new opportunities for the exploitation of microorganisms and animal and plant cells as producers or modifiers of chemical and biological products.This series of handbooks deals exclusively with microorganisms which are at the forefront of the new technologies and brings together in each of its volumes the background information necessary to appreciate the historical development of the organisms making up a particular genus, the degree to which molecular biology has opened up new opportunities, and the place they occupy in today's biotechnology industry. Our aim was to make this primarily a practical approach, with emphasis on methodology, combining for the first time information which has largely been spread across a wide literature base or only touched upon briefly in review articles. Each handbook should provide the reader with a source text, from which the importance of the genus to his or her work can be identified, and a practical guide to the handling and exploitation of the organisms included.It is perhaps apt that Volume I of the series should deal with a group of organisms involved in producing chemicals which have dominated the fermentation and pharmaceutical industries for the past forty years-the antibiotics. In terms of the degree to which molecular biology has made an impact on this genus to date, it is clear that the major rewards are still to come.

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“…A brief description of aspects of the chemistry of these two compounds and their derivatives provides a fitting backdrop for the chapters that follow (for a more thorough discussion of the chemistry of these antibiotics, see Cooper et al, 1973). A brief description of aspects of the chemistry of these two compounds and their derivatives provides a fitting backdrop for the chapters that follow (for a more thorough discussion of the chemistry of these antibiotics, see Cooper et al, 1973).…”

Section: Penicillin a N D Cephalosporin C H E M I S T R Y : A M I C Rmentioning

confidence: 99%

“…1-6;Rando, 1975). 1-8 (Allan et al, 1974;Cooper et al, 1973; RSOSi(CH 3 ) 3 By a combination of enzymatic and chemical reactions, penicillin can be hydrolyzed to the amino acid penicillamine (Eq.…”

Section: Penicillin a N D Cephalosporin C H E M I S T R Y : A M I C Rmentioning

confidence: 99%

Introduction

1978

Organic Chemistry: A Series of Monographs

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Chemical interconversion of the .beta.-lactam antibiotics

Cited by 47 publications

References 18 publications

Cephalosporins

Cephalosporins

Penicillium and Acremonium

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