Nucleoglycoconjugates: Design and Synthesis of a New Class of DNA–Carbohydrate Conjugates
Terry L. Sheppard Dr.
Departments of Chemistry and Molecular Biology and The Skaggs Institute for Chemical Biology The Scripps Research Institute 10550 North Torrey Pines Road La Jolla, CA 92037 (USA) Fax: (+858)-784-2943
Search for more papers by this authorChi-Huey Wong Prof.
Departments of Chemistry and Molecular Biology and The Skaggs Institute for Chemical Biology The Scripps Research Institute 10550 North Torrey Pines Road La Jolla, CA 92037 (USA) Fax: (+858)-784-2943
Search for more papers by this authorGerald F. Joyce Prof.
Departments of Chemistry and Molecular Biology and The Skaggs Institute for Chemical Biology The Scripps Research Institute 10550 North Torrey Pines Road La Jolla, CA 92037 (USA) Fax: (+858)-784-2943
Search for more papers by this authorTerry L. Sheppard Dr.
Departments of Chemistry and Molecular Biology and The Skaggs Institute for Chemical Biology The Scripps Research Institute 10550 North Torrey Pines Road La Jolla, CA 92037 (USA) Fax: (+858)-784-2943
Search for more papers by this authorChi-Huey Wong Prof.
Departments of Chemistry and Molecular Biology and The Skaggs Institute for Chemical Biology The Scripps Research Institute 10550 North Torrey Pines Road La Jolla, CA 92037 (USA) Fax: (+858)-784-2943
Search for more papers by this authorGerald F. Joyce Prof.
Departments of Chemistry and Molecular Biology and The Skaggs Institute for Chemical Biology The Scripps Research Institute 10550 North Torrey Pines Road La Jolla, CA 92037 (USA) Fax: (+858)-784-2943
Search for more papers by this authorThis work was supported by NASA and The Skaggs Institute for Chemical Biology at The Scripps Research Institute. T.L.S. was supported by a postdoctoral fellowship from the NASA Specialized Center for Research and Training in Exobiology.
Abstract
A solid-phase strategy for the synthesis of a new class of DNA–carbohydrate conjugates, termed nucleoglycoconjugates (see example shown), is presented. This phosphoramidite-based approach provides a general method to link carbohydrates within or at the termini of DNA oligonucleotides through stable phosphodiester bonds. The resulting glycoconjugates serve as substrates for enzymes used in the manipulation of DNA, and are effective as primers in extension reactions mediated by DNA polymerases, including the polymerase chain reaction.
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