Lewis AL, Toukach P, Bolton E, Chen X, Frank M, Lütteke T, Knirel Y, Schoenhofen I, Varki A, Vinogradov E, Woods RJ, Zachra N, Zhang J, Kamerling JP, Neelamegham S Cataloging natural sialic acids and other nonulosonic acids (NulOs), and their representation using the Symbol Nomenclature for Glycans Glycobiology33(2) (2023)
99-103
NCBI PubMed ID:36648443 Publication DOI:10.1093/glycob/cwac072 Journal NLM ID:9104124 Publisher: IRL Press at Oxford University Press Correspondence: S. Neelamegham <neelbuffalo.edu>; J.P. Kamerling <j.p.kamerlinguu.nl>; A.L. Lewis <a1lewishealth.ucsd.edu> Institutions: Complex Carbohydrate Research Center, University of Georgia, Athens, GA 30602, USA, Department of Chemistry, University of California, Davis, CA 95616, USA, Department of Obstetrics, Gynecology, and Reproductive Sciences, Glycobiology Research and Training Center, University of California, San Diego, CA 92093, USA, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow 119991, Russia, National Center for Biotechnology Information, National Library of Medicine, National Institutes of Health, Bethesda, MD 20894, USA, Biognos AB, Generatorsgatan 1/Box 8963, 402 74 Goteborg, Sweden, Institute of Veterinary Physiology and Biochemistry, Justus-Liebig-University Giessen, Frankfurter Str. 100, 35392 Giessen, Germany, Human Health Therapeutics Research Centre, National Research Council of Canada, Ottawa, ON K1A OR6, Canada, Department of Medicine and Cellular & Molecular Medicine, Glycobiology Research and Training Center, University of California, San Diego, CA 92093, USA, Department of Biological Chemistry, Johns Hopkins University School of Medicine, Baltimore, MD 21205, USA, Bijvoet Center, Utrecht University, 3584 CH Utrecht, The Netherlands, Department of Chemical & Biological Engineering, Biomedical Engineering and Medicine, State University of New York, Buffalo, NY 14260, USA
Nonulosonic acids or non-2-ulosonic acids (NulOs) are an ancient family of 2-ketoaldonic acids (alpha-ketoaldonic acids) with a 9-carbon backbone. In nature, these monosaccharides occur either in a 3-deoxy form (referred to as 'sialic acids') or in a 3,9-dideoxy 'sialic-acid-like' form. The former sialic acids are most common in the deuterostome lineage, including vertebrates, and mimicked by some of their pathogens. The latter sialic-acid-like molecules are found in bacteria and archaea. NulOs are often prominently positioned at the outermost tips of cell surface glycans, and have many key roles in evolution, biology and disease. The diversity of stereochemistry and structural modifications among the NulOs contributes to more than 90 sialic acid forms and 50 sialic-acid-like variants described thus far in nature. This paper reports the curation of these diverse naturally occurring NulOs at the NCBI sialic acid page (https://www.ncbi.nlm.nih.gov/glycans/sialic.html) as part of the NCBI-Glycans initiative. This includes external links to relevant Carbohydrate Structure Databases. As the amino and hydroxyl groups of these monosaccharides are extensively derivatized by various substituents in nature, the Symbol Nomenclature For Glycans (SNFG) rules have been expanded to represent this natural diversity. These developments help illustrate the natural diversity of sialic acids and related NulOs, and enable their systematic representation in publications and online resources.
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buffalo.edu>; J.P. Kamerling <j.p.kamerling