8 Functional Modifications and Nuclear Analogues of β-Lactam Antibiotics-Part I

Jaszberenyi, J. C.; Gunda, T. E.

doi:10.1016/s0079-6468(08)70181-4

Cited by 15 publications

(2 citation statements)

References 173 publications

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“…Ward (Glaxo Research Group, Greenford, Middx., U.K.) and cephalosporin C was a gift from Eli Lilly and Co. (Indianapolis, IN, U.S.A.). The methyl ester and the amide of benzylpenicillin were prepared as described by Jaszberenyi & Gunda (1975).…”

Section: Substratesmentioning

confidence: 99%

The importance of the negative charge of β-lactam compounds in the interactions with active-site serine dd-peptidases and β-lactamases

Varetto

Meester

Monnaie

et al. 1991

Biochemical Journal

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The interaction between various penicillins and cephalosporins the carboxylate group of which at C-3 or C-4 had been esterified or amidated and different penicillin-recognizing enzymes was studied. In general, our findings reinforced the common assumption that an anionic group at that position is necessary for the effective acylation of these enzymes. However, the relative activities of the modified beta-lactams as inactivators of the Streptomyces R61 DD-peptidase or as substrates of the Bacillus licheniformis, Streptomyces albus G and Enterobacter cloacae beta-lactamases did not fit a general scheme in which the intrinsic electronic and geometric properties of the beta-lactam compounds would be sufficient to explain their substrate or inactivator properties towards the various types of enzymes investigated.

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Section: Substratesmentioning

confidence: 99%

The importance of the negative charge of β-lactam compounds in the interactions with active-site serine dd-peptidases and β-lactamases

Varetto

Meester

Monnaie

et al. 1991

Biochemical Journal

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“…Hence the conformation depends on the two variable angles CP 2 and t{l 3 which determine the orienta tions of the aminoacyl substituent and the carboxyl grouping, respectively. A review on the functional modifi cations and nuclear analogues of ,B-Iactam antibiotics can be fo und in (17,18). Antibacterial activity (0) requires a ,B-lactam ring of sufficient strain and possibilities for electron delocalization outside the lactam ring; (b) appears to be associated with CP2 rotational angles ranging, in solution, between -180° and -160°, i.e.…”

Section: Scope and Limitationmentioning

confidence: 99%

Use of Model Enzymes in the Determination of the Mode of Action of Penicillins and Delta3-Cephalosporins

Ghuysen

Frère

Leyh‐Bouille

et al. 1979

Annu. Rev. Biochem.

114

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Von Isocyaniden via Vierkomponenten‐Kondensation zu Antibiotica‐Synthesen

Ugi

1982

Angewandte Chemie

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In memoriam 0110 BuyerDie Vierkomponenten-Kondensation von Aminen und Carbonylverbindungen mit Isocyaniden["'] und geeigneten Saure-Komponenten (Wasser, Thioschwefelsaure, Dihydrogenselenid, Hydrogenazid, Cyansaure, Thiocyansaure) zu a-Aminosaurederivaten wurde 1959 entdeckt. Dieses Reaktionsprinzip erinnert zugleich an die Strecker-Synthese und an die Passerini-Reaktion. Die Vierkomponenten-Kondensation ermoglicht leicht durchfiihrbare und ergiebige Eintopf-Synthesen vieler Arten komplizierter Molekiile aus einfachen Bausteinen. Erst seit wenigen Jahren werden die praparativen Vorziige der VierkomponentenKondensation bei Synthesen von Naturstoffen und ihrer Analoga durch zahlreiche Arbeitsgruppen ausgeniitzt, obwohl viele der Moglichkeiten, die dieses Syntheseprinzip eroffnet, seit mehr als zwanzig Jahren erkennbar waren. Im vorliegenden Fortschrittsbericht werden richtungsweisende Synthesen mannigfacher Antibiotica zusammenfassend erortert. Ihr Entwurf enthalt jeweils eine Vierkomponenten-Kondensation als Schliisselschritt, mit dem stufenreiche Reaktionsfolgen vermieden werden konnen, die sonst zum Erreichen des Syntheseziels erforderlich waren.

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8 Functional Modifications and Nuclear Analogues of β-Lactam Antibiotics-Part I

Cited by 15 publications

References 173 publications

The importance of the negative charge of β-lactam compounds in the interactions with active-site serine dd-peptidases and β-lactamases

The importance of the negative charge of β-lactam compounds in the interactions with active-site serine dd-peptidases and β-lactamases

Use of Model Enzymes in the Determination of the Mode of Action of Penicillins and Delta3-Cephalosporins

Von Isocyaniden via Vierkomponenten‐Kondensation zu Antibiotica‐Synthesen

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