Asymmetric Total Synthesis of C9′-epi-Sinefungin

Autor:	Matthew D. Shair, Rocco L. Policarpo, Danny T. C. Huang, Brandon A. Wright, Ludovic Decultot
Rok vydání:	2020
Předmět:	Methyltransferase 010405 organic chemistry Stereochemistry Chemistry Organic Chemistry Rational design Total synthesis 010402 general chemistry 01 natural sciences Biochemistry 0104 chemical sciences Stereocenter Overman rearrangement Sinefungin Epimer Physical and Theoretical Chemistry Nucleoside
Zdroj:	Organic Letters. 22:5594-5599
ISSN:	1523-7052 1523-7060
DOI:	10.1021/acs.orglett.0c01956
Popis:	The natural nucleoside (+)-sinefungin, structurally similar to cofactor S-adenosyl-L-methionine (SAM), inhibits various SAM-dependent methyltransferases (MTs). Access to sinefungin analogues could serve as the basis for the rational design of small-molecule methyltransferase inhibitors. We developed a route to the unnatural C9’ epimer of sinefungin that employed a diastereoselective Overman rearrangement to install the key C6’ amino stereocenter. The ability for late stage modification is highlighted, opening an avenue for the discovery of new MTs inhibitors.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::d06a6858d73dca3d6921fc67b30b152a https://doi.org/10.1021/acs.orglett.0c01956 Zobrazit plný text záznamu