Epithienamycins. II. Isolation and structure assignment.

Cassidy, Patrick J.; Albers-Schönberg, Georg; Goegelman, Robert T.; Miller, Thomas W.; Arison, Byron H.; Stapley, E. O.; Birnbaum, Jerome

doi:10.7164/antibiotics.34.637

Cited by 47 publications

(15 citation statements)

References 7 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Thienamycin was the first "carbapenem" and would eventually serve as the parent or model compound for all carbapenems. A series of other carbapenems were also identified (30,92,107,147,149,162,163,172,233); however, the discovery of thienamycin was paramount.…”

Section: In the Beginning…mentioning

confidence: 99%

Carbapenems: Past, Present, and Future

Papp-Wallace

Endimiani

Taracila

et al. 2011

Antimicrob Agents Chemother

1,181

962

View full text Add to dashboard Cite

In this review, we summarize the current "state of the art" of carbapenem antibiotics and their role in our antimicrobial armamentarium. Among the ␤-lactams currently available, carbapenems are unique because they are relatively resistant to hydrolysis by most ␤-lactamases, in some cases act as "slow substrates" or inhibitors of ␤-lactamases, and still target penicillin binding proteins. This "value-added feature" of inhibiting ␤-lactamases serves as a major rationale for expansion of this class of ␤-lactams. We describe the initial discovery and development of the carbapenem family of ␤-lactams. Of the early carbapenems evaluated, thienamycin demonstrated the greatest antimicrobial activity and became the parent compound for all subsequent carbapenems. To date, more than 80 compounds with mostly improved antimicrobial properties, compared to those of thienamycin, are described in the literature. We also highlight important features of the carbapenems that are presently in clinical use: imipenem-cilastatin, meropenem, ertapenem, doripenem, panipenem-betamipron, and biapenem. In closing, we emphasize some major challenges and urge the medicinal chemist to continue development of these versatile and potent compounds, as they have served us well for more than 3 decades.Carbapenems play a critically important role in our antibiotic armamentarium. Of the many hundreds of different ␤-lactams, carbapenems possess the broadest spectrum of activity and greatest potency against Gram-positive and Gram-negative bacteria. As a result, they are often used as "last-line agents" or "antibiotics of last resort" when patients with infections become gravely ill or are suspected of harboring resistant bacteria (23,(174)(175)(176)229). Unfortunately, the recent emergence of multidrug-resistant (MDR) pathogens seriously threatens this class of lifesaving drugs (189). Several recent studies clearly show that resistance to carbapenems is increasing throughout the world (35,64,73,123,151,155,173,200). Despite this menacing trend, our understanding of how to best use these agents is undergoing a renaissance, especially concerning their role with regard to ␤-lactamase inhibition. In this context, we view the number, type, and diversity of carbapenems as compelling reasons to explore these compounds for new insights into drug development.

show abstract

Section: In the Beginning…mentioning

confidence: 99%

Carbapenems: Past, Present, and Future

Papp-Wallace

Endimiani

Taracila

et al. 2011

Antimicrob Agents Chemother

1,181

962

View full text Add to dashboard Cite

show abstract

“…N-Acetylthienamycin has also been reported (64) to be produced in the same fermentation broth. Four additional isomeric N-acetylthienamycins were reported to be pro duced by Streptomyces flavogriseus and Streptomyces olivaceus (23,25,116). They have been identified as N-acetyl-6-epithienamycin (epithienamy ein A), N-acetyl-8-epithienamycin (epithienamyein C), and the dehydro analogues which are unsaturated in the N-acety1cysteamine side chain (epithienamycin B and D) (Table 5.)…”

Section: Occurrence Of Thienamycins and Related Substancesmentioning

confidence: 99%

Natural Beta-Lactam Antibiotics

Aoki¹,

Okuhara²

1980

Annu. Rev. Microbiol.

View full text Add to dashboard Cite

“…Although the importance of β-lactam antibiotics has been recognized for many years [ 330 , 428 – 431 ], the recent discovery of some structurally new types of compounds [ 432 – 437 ] has generated a flood of interest in their methods of synthesis. Of the many novel routes to the azetidinone ring inherent in these systems, the use of iron carbonyl complexes is an attractive and growing area of study [ 327 , 329 , 332 , 438 ].…”

Section: Synthesis Of Natural Products Via Iron Carbonylsmentioning

confidence: 99%

New chemical and stereochemical applications of organoiron complexes

Fatiadi

1991

J. RES. NATL. INST. STAN.

View full text Add to dashboard Cite

The objective of this review is to provide a current overview of the rapidly developing chemistry of organometallic complexes and particularly organoiron complexes useful in asymmetric and stereoselective reactions. Also covered are stereoselective reactions of α, β-unsaturated acyl ligands bound to the chiral auxiliary [(η5-C5H5) Fe(CO)(PPh3)] and new applications of organoiron complexes in the synthesis of natural products. The mechanistic aspects and stabilizing effects of the Fe(CO)3 group for alkenes or conjugated dienes are discussed. A brief summary of recent work on the special role of iron in biological reactions is also included.

show abstract

Epithienamycins. II. Isolation and structure assignment.

Cited by 47 publications

References 7 publications

Carbapenems: Past, Present, and Future

Carbapenems: Past, Present, and Future

Natural Beta-Lactam Antibiotics

New chemical and stereochemical applications of organoiron complexes

Contact Info

Product

Resources

About