Obstacles and solutions for chemical synthesis of syndecan-3 (53-62) glycopeptides with two heparan sulfate chains.
Proteoglycans play critical roles in many biological events. Due to their structural complexities, strategies towards synthesis of this class of glycopeptides bearing well-defined glycan chains are urgently needed. In this work, we give the full account of the synthesis of syndecan-3 glycopeptide (53-62) containing two different heparan sulfate chains. For assembly of glycans, a convergent 3+2+3 approach was developed producing two different octasaccharide amino acid cassettes, which were utilized towards syndecan-3 glycopeptides. The glycopeptides presented many obstacles for post-glycosylation manipulation, peptide elongation, and deprotection. Following screening of multiple synthetic sequences, a successful strategy was finally established by constructing partially deprotected single glycan chain containing glycopeptides first, followed by coupling of the glycan-bearing fragments and cleavage of the acyl protecting groups.
Department of Chemistry, Michigan State University, 578 S. Shaw Lane, East Lansing, MI 48824, USA.
Weizhun
W
Yang
Department of Chemistry, Michigan State University, 578 S. Shaw Lane, East Lansing, MI 48824, USA.
Keisuke
K
Yoshida
Department of Chemistry, Michigan State University, 578 S. Shaw Lane, East Lansing, MI 48824, USA.
Bo
B
Yang
Department of Chemistry, Michigan State University, 578 S. Shaw Lane, East Lansing, MI 48824, USA. Electronic address: xuefei@chemistry.msu.edu.
Xuefei
X
Huang
D006020:Glycopeptides / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D006497:Heparan Sulfate / Q000737:chemistry*; D015394:Molecular Structure; D053670:Syndecan-3 / Q000737:chemistry*
D006020:Glycopeptides; D006497:Heparan Sulfate; D053670:Syndecan-3
Carbohydrates; Glycopeptides; Glycosylation; Protecting groups; Synthesis design