Tautomeric modification of GIcNAc-thiazoline

Spencer Knapp; Mohannad Abdo; Kehinde Ajayi; Richard A. Huhn; Thomas J. Emge; Eun Ju Kim; John A. Hanover

doi:10.1021/ol0706814

Tautomeric modification of GIcNAc-thiazoline

Spencer Knapp, Mohannad Abdo, Kehinde Ajayi, Richard A. Huhn, Thomas J. Emge, Eun Ju Kim, John A. Hanover

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

39 Scopus citations

Abstract

The potent OGIcNAcase (OGA) inhibitor GIcNAc-thiazoline has been modified by buffer- or acylation-induced imine-to-enamine conversion and then electrophile or radical addition (X_n = D₃, F, N ₃, OH, SMe, COCF₃, CF₃). Several functionalized GIcNAc-thiazolines show highly selective inhibition of OGA vs human hexosaminidase and thus have promise as tools for targeted investigations of OGA, an enzyme linked to diabetes and neurodegeneration. A new radical addition/fragmentation reaction of the N-(trifluoroacetyl)enamine has been discovered.

Original language	English (US)
Pages (from-to)	2321-2324
Number of pages	4
Journal	Organic letters
Volume	9
Issue number	12
DOIs	https://doi.org/10.1021/ol0706814
State	Published - Jun 7 2007

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol0706814

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title = "Tautomeric modification of GIcNAc-thiazoline",

abstract = "The potent OGIcNAcase (OGA) inhibitor GIcNAc-thiazoline has been modified by buffer- or acylation-induced imine-to-enamine conversion and then electrophile or radical addition (Xn = D3, F, N 3, OH, SMe, COCF3, CF3). Several functionalized GIcNAc-thiazolines show highly selective inhibition of OGA vs human hexosaminidase and thus have promise as tools for targeted investigations of OGA, an enzyme linked to diabetes and neurodegeneration. A new radical addition/fragmentation reaction of the N-(trifluoroacetyl)enamine has been discovered.",

author = "Spencer Knapp and Mohannad Abdo and Kehinde Ajayi and Huhn, \{Richard A.\} and Emge, \{Thomas J.\} and Kim, \{Eun Ju\} and Hanover, \{John A.\}",

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doi = "10.1021/ol0706814",

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T1 - Tautomeric modification of GIcNAc-thiazoline

AU - Knapp, Spencer

AU - Abdo, Mohannad

AU - Ajayi, Kehinde

AU - Huhn, Richard A.

AU - Emge, Thomas J.

AU - Kim, Eun Ju

AU - Hanover, John A.

PY - 2007/6/7

Y1 - 2007/6/7

N2 - The potent OGIcNAcase (OGA) inhibitor GIcNAc-thiazoline has been modified by buffer- or acylation-induced imine-to-enamine conversion and then electrophile or radical addition (Xn = D3, F, N 3, OH, SMe, COCF3, CF3). Several functionalized GIcNAc-thiazolines show highly selective inhibition of OGA vs human hexosaminidase and thus have promise as tools for targeted investigations of OGA, an enzyme linked to diabetes and neurodegeneration. A new radical addition/fragmentation reaction of the N-(trifluoroacetyl)enamine has been discovered.

AB - The potent OGIcNAcase (OGA) inhibitor GIcNAc-thiazoline has been modified by buffer- or acylation-induced imine-to-enamine conversion and then electrophile or radical addition (Xn = D3, F, N 3, OH, SMe, COCF3, CF3). Several functionalized GIcNAc-thiazolines show highly selective inhibition of OGA vs human hexosaminidase and thus have promise as tools for targeted investigations of OGA, an enzyme linked to diabetes and neurodegeneration. A new radical addition/fragmentation reaction of the N-(trifluoroacetyl)enamine has been discovered.

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Tautomeric modification of GIcNAc-thiazoline

Abstract

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