N-Alkylated Analogues of Indolylthio Glycosides as Glycosyl Donors with Enhanced Activation Profile

Ganesh Shrestha; Matteo Panza; Yashapal Singh; Keith Stine; Alexei V. Demchenko

doi:10.1002/ejoc.202200300

N-Alkylated Analogues of Indolylthio Glycosides as Glycosyl Donors with Enhanced Activation Profile

Ganesh Shrestha, Matteo Panza, Yashapal Singh, Keith Stine, Alexei V. Demchenko

University of Missouri-St. Louis

Research output: Contribution to journal › Article › peer-review

Abstract

While studying indolylthio glycosides, previously we determined their activation profile that required large excess of activators. This drawback was partially addressed in the present study of N-alkylated SInR derivatives. The activation process was studied by NMR and the increased understanding of the mechanism led to a discovery of different activation pathways taking place with SIn versus SInR derivatives. Also investigated was orthogonality of the SInR leaving groups versus thioglycosides and selective activation of thioimidates over SInR glycosides.

Original language	American English
Journal	European Journal of Organic Chemistry
Volume	2022
DOIs	https://doi.org/10.1002/ejoc.202200300
State	Published - May 13 2022

Disciplines

Biochemistry, Biophysics, and Structural Biology

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title = "N-Alkylated Analogues of Indolylthio Glycosides as Glycosyl Donors with Enhanced Activation Profile",

abstract = " While studying indolylthio glycosides, previously we determined their activation profile that required large excess of activators. This drawback was partially addressed in the present study of N-alkylated SInR derivatives. The activation process was studied by NMR and the increased understanding of the mechanism led to a discovery of different activation pathways taking place with SIn versus SInR derivatives. Also investigated was orthogonality of the SInR leaving groups versus thioglycosides and selective activation of thioimidates over SInR glycosides. ",

author = "Ganesh Shrestha and Matteo Panza and Yashapal Singh and Keith Stine and Demchenko, {Alexei V.}",

year = "2022",

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language = "American English",

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T1 - N-Alkylated Analogues of Indolylthio Glycosides as Glycosyl Donors with Enhanced Activation Profile

AU - Shrestha, Ganesh

AU - Panza, Matteo

AU - Singh, Yashapal

AU - Stine, Keith

AU - Demchenko, Alexei V.

PY - 2022/5/13

Y1 - 2022/5/13

N2 - While studying indolylthio glycosides, previously we determined their activation profile that required large excess of activators. This drawback was partially addressed in the present study of N-alkylated SInR derivatives. The activation process was studied by NMR and the increased understanding of the mechanism led to a discovery of different activation pathways taking place with SIn versus SInR derivatives. Also investigated was orthogonality of the SInR leaving groups versus thioglycosides and selective activation of thioimidates over SInR glycosides.

AB - While studying indolylthio glycosides, previously we determined their activation profile that required large excess of activators. This drawback was partially addressed in the present study of N-alkylated SInR derivatives. The activation process was studied by NMR and the increased understanding of the mechanism led to a discovery of different activation pathways taking place with SIn versus SInR derivatives. Also investigated was orthogonality of the SInR leaving groups versus thioglycosides and selective activation of thioimidates over SInR glycosides.

UR - https://doi.org/10.1002/ejoc.202200300

U2 - 10.1002/ejoc.202200300

DO - 10.1002/ejoc.202200300

M3 - Article

VL - 2022

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

ER -

N-Alkylated Analogues of Indolylthio Glycosides as Glycosyl Donors with Enhanced Activation Profile

Abstract

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