Glycosyloxyamine Neoglycosylation: A Model Study Using Calicheamicin | Zendy

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

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Glycosyloxyamine Neoglycosylation: A Model Study Using Calicheamicin

Author(s) -

Goff Randal D.,

Singh Shanteri,

Thorson Jon S.

Publication year - 2011

Publication title -

chemmedchem

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.817

H-Index - 100

eISSN - 1860-7187

pISSN - 1860-7179

DOI - 10.1002/cmdc.201100028

Subject(s) - calicheamicin , bioconjugation , cytotoxicity , bioproduction , chemistry , combinatorial chemistry , computational biology , biochemistry , biology , in vitro , cancer research , myeloid leukemia

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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