- Total synthesis of vineomycin B2
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The first total synthesis of vineomycin B2 (1) has been accomplished. The aglycon segment, a vineomycinone B2 derivative, and the glycon segment, an α-l-acurosyl-l-rhodinose derivative, were prepared via C-glycosylation using an unprotected sugar and powerful chemoselective O-glycosylation using a 2,3-unsaturated sugar, respectively, as the key steps. Furthermore, effective and simultaneous introduction of the two glycon moieties to the aglycon part by concentration-controlled glycosylation led to the total synthesis of 1.
- Kusumi, Shunichi,Tomono, Satoshi,Okuzawa, Shunsuke,Kaneko, Erika,Ueda, Takashi,Sasaki, Kaname,Takahashi, Daisuke,Toshima, Kazunobu
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- Identification of the grincamycin gene cluster unveils divergent roles for GcnQ in different hosts, tailoring the L-rhodinose moiety
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The gene cluster responsible for grincamycin (GCN, 1) biosynthesis in Streptomyces lusitanus SCSIO LR32 was identified; heterologous expression of the GCN cluster in S. coelicolor M512 yielded P-1894B (1b) as a predominant product. The ΔgcnQ mutant accumulates intermediate 1a and two shunt products 2a and 3a bearing l-rhodinose for l-cinerulose A substitutions. In vitro data demonstrated that GcnQ is capable of iteratively tailoring the two l-rhodinose moieties into l-aculose moieties, supporting divergent roles of GcnQ in different hosts.
- Zhang, Yun,Huang, Hongbo,Chen, Qi,Luo, Minghe,Sun, Aijun,Song, Yongxiang,Ma, Junying,Ju, Jianhua
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supporting information
p. 3254 - 3257
(2013/07/26)
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