Expedient synthesis of core disaccharide building blocks from natural polysaccharides for heparan sulfate oligosaccharide assembly

Pawar, Nitin J.
Wang, Lei
Higo, Takuya
Bhattacharya, Chandrabali
Kancharla, Pavan K.
Zhang, Fuming
Baryal, Kedar
Huo, Chang Xin
Liu, Jian
Linhardt, Robert J.
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Biology , Chemistry and chemical biology , Chemical and biological engineering , Biomedical engineering
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Expedient synthesis of core disaccharide building blocks from natural polysaccharides for heparan sulfate oligosaccharide assembly, N. Pawar, L. Wang, T. Higo, C. Bhattacharya, P. K. Kancharla, F. Zhang, K. Baryal, C. -X. Huo, J. Liu, R. J. Linhardt, X. Huang, L. Hsieh-Wilson, Angewandte Chemie, 58, 18577 – 18583, 2019.
The complex sulfation motifs of heparan sulfate glycosaminoglycans (HS GAGs) play critical roles in many important biological processes. However, an understanding of their specific functions has been hampered by an inability to synthesize large numbers of diverse, yet defined, HS structures. Herein, we describe a new approach to access the four core disaccharides required for HS/heparin oligosaccharide assembly from natural polysaccharides. The use of disaccharides rather than monosaccharides as minimal precursors greatly accelerates the synthesis of HS GAGs, providing key disaccharide and tetrasaccharide intermediates in about half the number of steps compared to traditional strategies. Rapid access to such versatile intermediates will enable the generation of comprehensive libraries of sulfated oligosaccharides for unlocking the “sulfation code” and understanding the roles of specific GAG structures in physiology and disease.
Angewandte Chemie, 58, 18577 – 18583
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The Linhardt Research Labs.
The Shirley Ann Jackson, Ph.D. Center for Biotechnology and Interdisciplinary Studies (CBIS)
The Linhardt Research Labs Online Collection
Rensselaer Polytechnic Institute, Troy, NY
Angewandte Chemie - International Edition
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