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

chunyang shen; Haixin Ding; Xueping Tao; Ruchun Yang; Jiang Bai; Banpeng Cao; Yiyuan Peng; Qiang Xiao

doi:10.3762/bxiv.2019.128.v1

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

chunyang shen ,
Haixin Ding ,
Xueping Tao ,
Ruchun Yang ,
Jiang Bai ,
Banpeng Cao ,
Yiyuan Peng and
Qiang Xiao

Submitting author affiliation:

Jiangxi Science & Technology Normal University, Nanchang, China

Beilstein Arch. 2019, 2019128. https://doi.org/10.3762/bxiv.2019.128.v1

Published 23 Oct 2019

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Show All Preprints Nanotechnology Organic chemistry Bioorganic chemistry / chemical biology Catalysis Chemical methods and reactions Flow and process chemistry Green and sustainable chemistry Materials chemistry Medicinal and pharmaceutical chemistry Nano- and molecular-scale electronics Nano-biomaterials and bioscience Nanomagnetics Nanomaterials, thin films and nanointerfaces Nanomedicine Nanometrology and nanomechanics Nano-optics Nanopatterning, self-assembly and nanofabrication Nanostructures for energy and sensing applications Natural products chemistry Organo main group chemistry Other nanotechnology (unclassified) Other organic chemistry (unclassified) Photochemistry and photovoltaics Physical organic chemistry Supramolecular chemistry

Abstract

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.

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When a peer-reviewed version of this preprint is available, this information will be updated in the information box above. If no peer-reviewed version is available, please cite this preprint using the following information:

shen, C.; Ding, H.; Tao, X.; Yang, R.; Bai, J.; Cao, B.; Peng, Y.; Xiao, Q. Beilstein Arch. 2019, 2019128. doi:10.3762/bxiv.2019.128.v1

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aromatic	the word “aromatic”
aromatic aldehyde	the word “aromatic” OR “aldehyde”
+aromatic +aldehyde	both words “aromatic” AND “aldehyde”
+aromatic -aldehyde	the word “aromatic” but NOT “aldehyde”
“aromatic aldehyde”	the exact phrase “aromatic aldehyde”
benz*	words which begin with “benz”, such as “benzene” or “benzyl”
benz*yl	words that begin with “benz” and end with “yl”, such as “benzyl” or “benzoyl”
benzyl~	words that are close to the word “benzyl”, such as “benzoyl” (i.e., fuzzy search)