Non-enzymatic synthesis of <i>C</i>-methylated fluostatins: discovery and reaction mechanism.

De, Bidhan Chandra; Yang, Chunfang; Huang, Chunshuai; Zhang, Changsheng; Zhang, Wenjun

Non-enzymatic synthesis of C-methylated fluostatins: discovery and reaction mechanism.

De, Bidhan Chandra; Yang, Chunfang; Huang, Chunshuai; Zhang, Changsheng; Zhang, Wenjun.

De BC; Key Laboratory of Tropical Marine Bioresources and Ecology, Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology Chinese Academy of Sciences, Guangzhou 510301, China. wzhang@scsio.ac.cn.
Yang C; University of Chinese Academy of Sciences, 19 Yuquan Road, Beijing 100049, China.
Huang C; Key Laboratory of Tropical Marine Bioresources and Ecology, Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology Chinese Academy of Sciences, Guangzhou 510301, China. wzhang@scsio.ac.cn.
Zhang C; University of Chinese Academy of Sciences, 19 Yuquan Road, Beijing 100049, China.
Zhang W; Key Laboratory of Tropical Marine Bioresources and Ecology, Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology Chinese Academy of Sciences, Guangzhou 510301, China. wzhang@scsio.ac.cn.

Org Biomol Chem ; 22(6): 1152-1156, 2024 02 07.

Article en En | MEDLINE | ID: mdl-38214554

ABSTRACT

ABSTRACT

Two C-methylated fluostatins (FSTs) B3 (1) and B4 (2) were synthesized from flavin-mediated nonenzymatic epoxide ring-opening reactions of FST C. The structures of 1 and 2 were elucidated by HRESIMS, NMR, and ECD spectroscopic analyses. A subsequent 13C labeling study demonstrated that the C-methyl groups of 1 and 2 were derived from DMSO and enabled the mechanistic proposal of a nonenzymatic C-methylation.

Asunto(s)

Metilación; Espectroscopía de Resonancia Magnética

Texto completo

Imprimir

XML

PubMed Links

Search on Google