Synthesis and applications of alkylated C-sugars as peptide bioconjugates

Permethylated C-sugars affect the stability and solubility of their carbohydrate precursors and may represent an important group of bioconjugates. When properly functionalized, these unitscan be appended to the N- and C-termini or to the side chains ofpeptides or other therapeutic candidates. In this report, we describe the synthesis of an amine-functionalized alkylated mannose derivative and confirm the configuration by determiningthe X-ray crystal structure of its nitrile precursor. An acid functionalized counterpart, when attached to the N-terminus of aNR box peptide analog, improved binding to estrogen receptor (ER) but not to ER.