Total Synthesis of the Antibiotic Branimycin

Marchart, Stefan; Gromov, Alexey; Mulzer, Johann

doi:10.1002/anie.200906453

Cited by 25 publications

(16 citation statements)

References 28 publications

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“…3 Since then, there was a great interest in this new molecule, and a couple of organic syntheses have been developed. 4,5 Recently, the semisynthesis of branimycin derivatives has been reported in a patent, 6 demonstrating Avileś Canyon up to m depth. 10−13 One of these strains, Pseudonocardia carboxydivorans M-227, isolated at 3000 m depth in the water column, was further studied.…”

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confidence: 99%

Branimycins B and C, Antibiotics Produced by the Abyssal Actinobacterium Pseudonocardia carboxydivorans M-227

et al. 2017

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family of macrolide antibiotics known as nargenicins, 30 which exhibit antimicrobial activity mainly against Staph-31 ylococcus aureus. Nargenicins and branimycins have a tricyclic 32 structure with either a 9-or 10-membered lactone ring and 33 contain a unique ether bridge. In 1977, the first members of the 34 nargenicin family were isolated by Pfizer and Upjohn after the 35 aerobic fermentation of Nocardia argentinensis ATCC 31306. 36 This family of compounds and their antibacterial activity were 37 later patented, 1 and the structure of one of them, nargenicin 38 A1, was elucidated.2 Although it showed antibacterial activity in 39 vitro, this was restricted to Gram-positive bacteria, particularly 40 methicillin-resistant S. aureus (MRSA). It was also described 41 that nargenicin A1 induces cell differentiation and can be used, 42 therefore, as a possible treatment for neoplastic diseases. 43The first branimycin (1) was isolated in 1998 from the 44 Actinomycete GW 60/1571 and its structure determined by the 45

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Branimycins B and C, Antibiotics Produced by the Abyssal Actinobacterium Pseudonocardia carboxydivorans M-227

et al. 2017

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“…The second oxa-bridged macrolide to succumb to total synthesis is branimycin reported by Mulzer et al in 2010. [22] The retrosynthetic analysisi ss hown in Scheme 6. The key disconnection is similar to that for nargenicin A1 (2).…”

Section: Total Synthesis Of Branimycin (4)mentioning

confidence: 99%

“…[21] Interestingly,a lmost3 0y ears after the initial discoveryo f1,t he branimycins (4-7)w ere identified and these are the only members of the group with a 9-membered macrolactone ring. [22][23][24] To date, nargenicin family antibioticshave been isolated from ar ange of bacterial species including Pseudonocardia, Saccharothrix, Actinoplanes, Nocardioides, Saccharopolyspora and Streptomyces species, all of which are members of the Actinobacteria,awell-known powerhouse for natural product biosynthesis. [15,18,19,23,25] Several synthetic studies of these molecules have been attempted, which have resulted in the total synthesis of (+ +)-18deoxynargencin A1 [26] and branimycin A.…”

Section: The Nargenicin Antibioticsmentioning

confidence: 99%

The Nargenicin Family of Oxa‐Bridged Macrolide Antibiotics

Pidot

Rizzacasa

2019

Chemistry A European J

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The nargenicin family of antibiotic macrolides comprise a group of bacterial natural products with a rare ether bridged cis‐decalin moiety and a narrow spectrum of activity. Most family members were identified almost four decades ago and were placed on the shelf due to the numbers of broad‐spectrum compounds available at the time. However, in light of rising rates of antimicrobial resistance, there has been a renewed interest in the use of narrow‐spectrum antimicrobials. Here, we review the history of this family of compounds, including synthetic approaches, and highlight the recently uncovered genetic basis for nargenicin production. Given the renewed pharmaceutical interest in these compounds, we also investigate structure–activity relationships among these molecules, with a view to the future development of members of this unusual antibiotic family.

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“…In the approach to branimycin developed in by Mulzer group, (Marchart, 2010) the target molecule was retrosynthetically disconnected at the bridgehead position and at the lactone group to give the octalin fragment 44 and polyketid unit 46.…”

Section: Virginiamycin Mmentioning

confidence: 99%