Glycosyloxyamine neoglycosylation: A model study using calicheamicin

Randal D. Goff; Shanteri Singh; Jon S. Thorson

doi:10.1002/cmdc.201100028

Glycosyloxyamine neoglycosylation: A model study using calicheamicin

Randal D. Goff, Shanteri Singh, Jon S. Thorson

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

10 Scopus citations

Abstract

Sweetness & light! The glycosyloxyamine glycoside of calicheamicin was exploited to form neo-D-ribosides in one efficient chemoselective step. Assessment of the neoglycosides revealed only slight reductions in cytotoxicity or ability to cleave DNA compared to the parent aglycons. This study exposes a previously unrecognized method for efficient calicheamicin bioconjugation amenable to a wide range of cancer- selective targeting modalities.

Original language	English
Pages (from-to)	774-776
Number of pages	3
Journal	ChemMedChem
Volume	6
Issue number	5
DOIs	https://doi.org/10.1002/cmdc.201100028
State	Published - May 2 2011

Keywords

Carbohydrates
Enediynes
Glycosides
Glycosylation
Natural products

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Pharmacology
Drug Discovery
Pharmacology, Toxicology and Pharmaceutics (all)
Organic Chemistry

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1002/cmdc.201100028

Cite this

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abstract = "Sweetness & light! The glycosyloxyamine glycoside of calicheamicin was exploited to form neo-D-ribosides in one efficient chemoselective step. Assessment of the neoglycosides revealed only slight reductions in cytotoxicity or ability to cleave DNA compared to the parent aglycons. This study exposes a previously unrecognized method for efficient calicheamicin bioconjugation amenable to a wide range of cancer- selective targeting modalities.",

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author = "Goff, {Randal D.} and Shanteri Singh and Thorson, {Jon S.}",

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doi = "10.1002/cmdc.201100028",

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T2 - A model study using calicheamicin

AU - Goff, Randal D.

AU - Singh, Shanteri

AU - Thorson, Jon S.

PY - 2011/5/2

Y1 - 2011/5/2

N2 - Sweetness & light! The glycosyloxyamine glycoside of calicheamicin was exploited to form neo-D-ribosides in one efficient chemoselective step. Assessment of the neoglycosides revealed only slight reductions in cytotoxicity or ability to cleave DNA compared to the parent aglycons. This study exposes a previously unrecognized method for efficient calicheamicin bioconjugation amenable to a wide range of cancer- selective targeting modalities.

AB - Sweetness & light! The glycosyloxyamine glycoside of calicheamicin was exploited to form neo-D-ribosides in one efficient chemoselective step. Assessment of the neoglycosides revealed only slight reductions in cytotoxicity or ability to cleave DNA compared to the parent aglycons. This study exposes a previously unrecognized method for efficient calicheamicin bioconjugation amenable to a wide range of cancer- selective targeting modalities.

KW - Carbohydrates

KW - Enediynes

KW - Glycosides

KW - Glycosylation

KW - Natural products

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JF - ChemMedChem

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ER -

Glycosyloxyamine neoglycosylation: A model study using calicheamicin

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

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