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. 2016 Dec 2;81(23):12052-12059.
doi: 10.1021/acs.joc.6b02441. Epub 2016 Nov 10.

Homoserine as an Aspartic Acid Precursor for Synthesis of Proteoglycan Glycopeptide Containing Aspartic Acid and a Sulfated Glycan Chain

Weizhun Yang  1 , Sherif Ramadan  1   2 , Bo Yang  1 , Keisuke Yoshida  1 , Xuefei Huang  1
Affiliations

Homoserine as an Aspartic Acid Precursor for Synthesis of Proteoglycan Glycopeptide Containing Aspartic Acid and a Sulfated Glycan Chain

Weizhun Yang et al. J Org Chem. .

Abstract

Among many hurdles in synthesizing proteoglycan 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 first time that a glycopeptide containing aspartic acid and an O-sulfated glycan was synthesized.

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Conflict of interest statement

Notes: The authors declare no competing financial interest.

Figures

Figure 1
Figure 1
Benzyl ester protected Asp forms undesired aspartimide side products during glycopeptide synthesis.
Figure 2
Figure 2
Proposed intermediates and mechanism for homoserine oxidation.
Scheme 1
Scheme 1
Synthesis of dipeptide 1.
Scheme 2
Scheme 2
Synthesis of glycopeptide 16 using the homoserine strategy.
Scheme 3
Scheme 3
Synthesis of O-sulfated glycopeptide 24 using the homoserine strategy.
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