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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.