By Robert B. Morin, Marvin Gorman
Chemistry and Biology of ?-Lactam Antibiotics, quantity 1: Penicillins and Cephalosporins presents details pertinent to the learn of antibiotics containing the ?-lactam moiety. This e-book discusses the incidence of a bunch of ?-lactam antibiotics structurally on the topic of cephalosporin C.
Organized into 5 chapters, this quantity starts off with an outline of the mechanism of motion of ?-lactam antibiotics that prompted many microbiologists to strengthen screening instruments for the detection of the ?-lactam moiety. this article then discusses the invention of the nocardicins, the thienamycins, and olivanic acids. different chapters offer a precis of the fundamental penicillin sulfoxide chemistry that gave upward push to many compounds. This publication discusses besides the power of chemists to foretell the extent of organic job of a compound from wisdom of its constitution via theoretical and physicochemical reports. the ultimate bankruptcy offers with quantitative structure–activity relationships.
This publication is a worthy source for microbiologists, chemists, and scientists.
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Additional info for Penicillins and Cephalosporins
1980). Fleming's discovery. Reviews of Infectious Diseases 2 (1), 1 4 0 - 1 4 1 . Abraham, E. , and Florey, H. W. (1971). Biographical Memoirs of Fellows of the Royal Society 17, 2 5 5 - 3 0 2 . Clark, H. T . , Johnson, J. , e d s . (1949). " Princeton University Press, Princeton, N e w Jersey. Florey, H. , Chain, E . , Heatley, N . , Jennings, Μ. Α . , Sanders, A. , Abraham, E . , and Florey, Ν . E. (1949). "Antibiotics," Vol. 2. Oxford University Press, Oxford. Flynn, Ε. H . , ed. (1972). "Cephalosporins and Penicillins: Chemistry and B i o l o g y .
This isomeric mixture could be reduced to the single sulfide (109). The double bond was isomerized to the α,β-unsaturated compound 110 which on progressive ozonolysis first produced the thiooxalate (111) and then the oxamide (112). Treatment of 107 and 108 with triethylamine resulted in the cyclized product (113). Use of the penicillin sulfoxide methyl ester (114) gave the same mixture of sulfoxide epimers which could then be separated (115 and 116). Base treatment of the separated isomers showed that 115 cy- 25 THE CHEMISTRY OF PENICILLIN SULFOXIDE C 0 2C H 2C 6H 4p N 0 2 (87) clized to 117; whereas 116 gave only the double bond isomer (118).
Reactions of Sulfoxide Equivalents Chemistry and Biology of ß-Lactam Antibiotics, Vol. 1 2 3 3 9 14 17 24 29 31 39 46 48 49 50 53 53 57 59 62 64 67 68 72 72 72 74 77 78 78 Copyright © 1982 by Academic Press, Inc. All rights of reproduction in any form reserved. ISBN 0-12-506301-6 1 2 ROBIN D. G. COOPER AND GARY Α. KOPPEL IX. I. 83 83 87 88 Cephalosporin Chemistry A. Utilization of the 3-Exomethylenecepham B. N o n a q u e o u s Displacement References Introduction The sulfoxide of a penicillin was first prepared over 30 years ago during the structural investigations of this exciting new therapeutic discovery (Peck and Folkers, 1949).