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Originally published In Press as doi:10.1074/jbc.M202034200 on June 21, 2002

J. Biol. Chem., Vol. 277, Issue 36, 33456-33467, September 6, 2002
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Characterization of a Heparan Sulfate Octasaccharide That Binds to Herpes Simplex Virus Type 1 Glycoprotein D*

Jian Liuab, Zach Shriverc, R. Marshall Poped, Suzanne C. Thorpa, Michael B. Duncanae, Ronald J. Copelandaf, Christina S. Raskag, Keiichi Yoshidah, Roselyn J. Eisenbergi, Gary Cohenj, Robert J. Linhardtk, and Ram Sasisekharanc

From the a Division of Medicinal Chemistry and Natural Products, School of Pharmacy, University of North Carolina, Chapel Hill, North Carolina 27599, the c Biological Engineering Division, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, the d Proteomic Core Facility, Department of Biochemistry, University of North Carolina, Chapel Hill, North Carolina 27599, the g Department of Chemistry, University of North Carolina, Chapel Hill, North Carolina 27599, the h Tokyo Research Institute of Seikagaku Corporation, Higashiyamato-shi, Tokyo 207, Japan, the i Center for Oral Health Research and School of Veterinary Medicine, University of Pennsylvania, Philadelphia, Pennsylvania 19104, the j School of Dental Medicine and Center for Oral Health Research, University of Pennsylvania, Philadelphia, Pennsylvania 19104, and the k Department of Chemistry, University of Iowa, Iowa City, Iowa 52242

Herpes simplex virus type 1 utilizes cell surface heparan sulfate as receptors to infect target cells. The unique heparan sulfate saccharide sequence offers the binding site for viral envelope proteins and plays critical roles in assisting viral infections. A specific 3-O-sulfated heparan sulfate is known to facilitate the entry of herpes simplex virus 1 into cells. The 3-O-sulfated heparan sulfate is generated by the heparan sulfate D-glucosaminyl-3-O-sulfotransferase isoform 3 (3-OST-3), and it provides binding sites for viral glycoprotein D (gD). Here, we report the purification and structural characterization of an oligosaccharide that binds to gD. The isolated gD-binding site is an octasaccharide, and has a binding affinity to gD around 18 µM, as determined by affinity coelectrophoresis. The octasaccharide was prepared and purified from a heparan sulfate oligosaccharide library that was modified by purified 3-OST-3 enzyme. The molecular mass of the isolated octasaccharide was determined using both nanoelectrospray ionization mass spectrometry and matrix-assisted laser desorption/ionization mass spectrometry. The results from the sequence analysis suggest that the structure of the octasaccharide is a heptasulfated octasaccharide. The proposed structure of the octasaccharide is Delta UA-GlcNS-IdoUA2S-GlcNAc-UA2S-GlcNS-IdoUA2S-GlcNH23S6S. Given that the binding of 3-O-sulfated heparan sulfate to gD can mediate viral entry, our results provide structural information about heparan sulfate-assisted viral entry.

* This work is supported in part by National Institutes of Health Grants AI50050-01 (to J. L.), CA 090940 and GM 57073 (to R. S.), and the Burroughs Wellcome Foundation (to R. S.). Some preliminary experiments were carried out in the laboratory of R. Rosenberg, which is supported by National Institutes of Health Grants R01 HL 59479 and P01 HL 41484.The costs of publication of this article were defrayed in part by the payment of page charges. The article must therefore be hereby marked "advertisement" in accordance with 18 U.S.C. Section 1734 solely to indicate this fact.

b To whom correspondence and reprint requests should be addressed: Rm. 309, Beard Hall, CB 7360, University of North Carolina, Chapel Hill, NC 27599. Tel.: 919-843-6511; Fax: 919-843-5432; E-mail: jian_liu@unc.edu.

e Recipient of Predoctoral Fellowship 2001-17095 from The David and Lucile Packard Foundation.

f Recipient of Predoctoral Fellowship 2001-17094 from The David and Lucile Packard Foundation.

Copyright © 2002 by The American Society for Biochemistry and Molecular Biology, Inc.
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