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Published December 16, 2019 | Accepted Version + Supplemental Material
Journal Article Open

Expedient Synthesis of Core Disaccharide Building Blocks from Natural Polysaccharides for Heparan Sulfate Oligosaccharide Assembly

Abstract

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. Here, we describe a new approach to access the four core disaccharides required for HS/heparin oligosaccharide assembly from natural polysaccharides. The use of disaccharides as minimal precursors rather than monosaccharides 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.

Additional Information

© 2019 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim. Manuscript received: July 15, 2019; Revised manuscript received: August 22, 2019; Accepted manuscript online: September 25, 2019; Version of record online: November 6, 2019. Financial support was provided by the NIH Common Fund grant U01 GM116262-03 and the NIH R01 grant HL62244. We thank Dr. Mona Shahgholi in the CCE Division Mass Spectrometry Facility and Dr. David Vander Velde in the CCE Division NMR Facility at Caltech. The authors declare no conflict of interest.

Attached Files

Accepted Version - nihms-1052528.pdf

Supplemental Material - anie201908805-s1-pawar_hsiehwilson_supporting_information_angew_accepted.pdf

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August 22, 2023
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