Total synthesis of 2'-O-methyl-β-l-arabinosyluridine and reassignment the nucleoside from penicillium sp. as 2'-O-methyl-β-l-uridine

[Display omitted] •Reassignment the nucleoside from Penicillium sp. as 2′-O-methyl-β-l-uridine.•Total synthesis of the first reported naturally occurring l-nucleoside.•Total synthesis of 2′-O-methyl-β-l-arabinosyluridine. In order to validate the structure of a rarely reported naturally occurring nu...

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Bibliographic Details
Published in:Phytochemistry letters 2020-04, Vol.36, p.68-72
Main Authors: Shen, Chunyang, Ding, Haixin, Tao, Xueping, Yang, Ruchun, Bai, Jiang, Cao, Ban-Peng, Peng, Yi-Yuan, Xiao, Qiang
Format: Article
Language:English
Subjects:
2'-O-methyl-β-l-uridine
l-arabinosyluridine
Naturally occurring nucleoside
Penicillium sp
Total synthesis
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Summary:[Display omitted] •Reassignment the nucleoside from Penicillium sp. as 2′-O-methyl-β-l-uridine.•Total synthesis of the first reported naturally occurring l-nucleoside.•Total synthesis of 2′-O-methyl-β-l-arabinosyluridine. In order to validate the structure of a rarely reported naturally occurring nucleoside isolated from the broth of Penicillium sp. (NO. 64), practical syntheses of 2′-O-methyl-β-l-arabinosyluridine, 2′-O-methyl-α-l-arabinosyluridine, and 2′-O-methyl-β-l-uridine were accomplished. Comparing their nuclear magnetic resonance (NMR) spectra and physical data, its structure was reassigned as 2′-O-methyl-β-l-uridine instead of former reported 2′-O-methyl-β-l-arabinosyluridine.
ISSN:1874-3900
1876-7486
DOI:10.1016/j.phytol.2020.01.018