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Homoserine as an Aspartic Acid Precursor for Synthesis of Proteoglycan Glycopeptide Containing Aspartic Acid and a Sulfated Glycan Chain
The Journal of Organic Chemistry • 2016
Publication Information
Authors
Weizhun Yang,
Sherif Ramadan,
Bo Yang,
Keisuke Yoshida,
and Xuefei Huang
Keywords
Glycopeptide, Sulfation, Stereoselectivity.
Journal
The Journal of Organic Chemistry
Publisher
ACS Publications
Volume
81
Issue
23
Pages
12052 − 12059
publication.type
International
Paper Link
Open Link
Supplementary Materials
Not Available
Abstract
Among many hurdles in synthesizing proteo-
glycan glycopeptides, one challenge is the incorporation of
aspartic acid in the peptide backbone and acid sensitive
O
-
sulfated glycan chains. To overcome this, a new strategy was
developed utilizing homoserine as an aspartic acid precursor.
The conversion of homoserine to aspartic acid in the
glycopeptide was successfully accomplished by late stage
oxidation using (2,2,6,6-tetramethyl-piperidin-1-yl)oxyl
(TEMPO) and bis(acetoxy)iodobenzene (BAIB). This is the
fi
rst time that a glycopeptide containing aspartic acid and an
O-sulfated glycan was synthesized.
glycan glycopeptides, one challenge is the incorporation of
aspartic acid in the peptide backbone and acid sensitive
O
-
sulfated glycan chains. To overcome this, a new strategy was
developed utilizing homoserine as an aspartic acid precursor.
The conversion of homoserine to aspartic acid in the
glycopeptide was successfully accomplished by late stage
oxidation using (2,2,6,6-tetramethyl-piperidin-1-yl)oxyl
(TEMPO) and bis(acetoxy)iodobenzene (BAIB). This is the
fi
rst time that a glycopeptide containing aspartic acid and an
O-sulfated glycan was synthesized.