Asymmetric synthesis of macrolactin analogue

Kobayashi, Yusuke; Fukuda, Akira; Kimachi, Tetsutaro; Ju‐ichi, Motoharu; Takemoto, Yoshiji

doi:10.1016/j.tetlet.2003.11.055

Cited by 22 publications

(15 citation statements)

References 33 publications

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“…Takemoto and co-workers have reported the enantioselective synthesis of macrolactin A analogues in which an alkyne to 1,3-diene isomerization was used to prepare a key intermediate (Scheme 22). 43,44 In this case, the formed (E,E)-1,3-diene itself is a structural element of the final product and the activating carbonyl group is reduced to a chiral alcohol. In this work the optimal catalyst for the isomerization of alkynone 49 was found to be bis(diphenylphosphine)butane (DPPB), rather than triphenylphosphine.…”

Section: Scheme 17mentioning

confidence: 99%

The Phosphine-Catalyzed Alkyne to 1,3-Diene Isomerization Reaction

Kwong¹,

Fu²,

Lam³

et al. 2008

Synthesis

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Section: Scheme 17mentioning

confidence: 99%

The Phosphine-Catalyzed Alkyne to 1,3-Diene Isomerization Reaction

Kwong¹,

Fu²,

Lam³

et al. 2008

Synthesis

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“…So far, at least 30 MLNs have been reported, among which macrolactin A (MLN A, 1a) and 7-O-succinyl macrolactin A (SMA) are at present in preclinical evaluation as antimacular degeneration and antitumor agents (Bae et al, 2014). Due to their promising bioactivity and unique structure, many efforts have been devoted to chemical syntheses of MLNs (Smith and Ott, 1998;Marino et al, 2002;Kobayashi et al, 2004). Bacillaenes (BAEs) are polyene antibiotics originally discovered from the fermentation broth of Bacillus subtilis as bacteriostatic agents (Patel et al, 1995) (Fig.…”

Section: Introductionmentioning

confidence: 99%

Genome‐wide identification and characterization of macrolide glycosyltransferases from a marine‐derived Bacillus strain and their phylogenetic distribution

Liu

Qin

Liu

et al. 2016

Environmental Microbiology

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Clarifying glycosyltrasferases (GTs) function is of significance for the development of GT inhibitors as drugs, and the use of GTs to glycodiversify small molecules in the search of drug leads. While many Actinomyces natural-product GTs had been functionally characterized, our understanding towards Bacillus natural-product GTs is so far very limited. Herein, genome-wide identification of macrolide GT genes from marine-derived Bacillus methylotrophicus B-9987 revealed the presence of three macrolide GT genes bmmGT1-3. While bmmGT1 was previously revealed to be involved in the biosynthesis of trans-acyltransferase (AT) polyketides compounds macrolactins (MLNs) and bacillaenes (BAEs), the functions of bmmGT2 and bmmGT3 were probed, demonstrating that they are capable to biochemically catalyze glycosylation of MLNs and BAEs as well but interestingly with different regioselectivity, affording four new MLNs analogs. Notably, further genome mining revealed that the orthologs of these three macrolide GT genes showed a regular distribution in the subtilis- and the cereus-clade Bacillus strains; interestingly, bmmGT1 orthologs only occurred in the subtilis-clade Bacillus, and they were also found in the genomes of Streptomyces strains, suggesting their close phylogenetic relationship. These results provide the first significant insight into the important roles of Bacillus macrolide GTs in the biology of the species.

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“…sunhua in the soil of a potato cultivation area (5) and was produced by a soil Streptomyces species (6) and by Bacillus amyloliquefaciens FZB42 (7). Because of their unreliable supply from cell culture, structural uniqueness, and broad therapeutic potential, MA and macrolactin analogs have been attractive targets for asymmetric syntheses (8). Indeed, macrolactins A and E have been chemically synthesized (9)(10)(11).…”

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confidence: 99%

“…MA and SMA also exhibited excellent antibacterial activities on intestinal vancomycin-resistant enterococci colonization in mice (4). MA has a broad spectrum of activity, with significant antiviral and cancer cell cytotoxic properties, including inhibition of B16-F10 murine melanoma cell replication and mammalian herpes simplex viruses (1,8). MA has been shown to protect lymphoblast cells against HIV by inhibiting viral replication (1).…”

mentioning

confidence: 99%