Nomenclature carbohydrate

Trivial names are common in carbohydrate nomenclature. Fifteen of them form the basis of the systematic nomenclature. They are assigned to the simple aldoses (polyhydroxyaldehydes), from triose to hexoses. 

Hexoses allose, altrose, galactose, glucose, gulose, idose, mannose, talose 

Among the keto-hexoses, fructose is of major natural occurrence. 

Names of cyclised (hemi-acetalised) aldoses and ketoses contain the infixes pyran or furan to indicate the six- or five-membered heterocyclic structure and a stereodescriptor, a or p, to indicate the configuration of the anomeric or hemi-acetal carbon atom. 

Although the names of the saccharides are generally trivial, systematic nomenclature is used to name their derivatives. Because trivial names are not amenable to the treatments usually applied to the names of ordinary parent hydrides, many adaptations are necessary and some peculiarities must be noted. 

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Complications arising from other types of isomerism. Positional and geometrical isomerism, also described in Sec. 1.6, will be excluded for simplicity. In actual polymers these are not always so easily ignored. Polymerization of 1,2-disubstituted ethylenes. Since these introduce two different asymmetric carbons into the polymer backbone (second substituent Y), they have the potential to display ditacticity. Our attention to these is limited to the illustration of some terminology which is derived from carbohydrate nomenclature (structures [IX]-[XII]) ... 

For a first-person account of the development of systematic carbohydrate nomenclature see C. D. Hurd s article in the December 1989 issue of the Journal of Chemical Education, pp. 984-988. 

American Chemical Society Committee for Carbohydrate Nomenclature D. Horton (Chairman), L. Anderson, D.C. Baker, H.H. Baer, J.N. BeMiller, B. Bossenbroek, R. W. Jeanloz, K.L. Loening, W. A. Szarek, R.S. Tipson, W.J. Whelan, R.L. Whistler. 

Carb-O. Historical development of carbohydrate nomenclature 0.1. Early approaches 0.2. The contribution of Emil Fischer 0.3. Cyclic forms 0.4. Nomenclature commissions 2-Carb-l. Definitions and conventions... 

These Recommendations expand and replace the Tentative Rules for Carbohydrate Nomenclature [1] issued in 1969 jointly by the IUPAC Commission on the Nomenclature of Organic Chemistry and the IUB-IUPAC Commission on Biochemical Nomenclature (CBN) and reprinted in [2]. They also replace other published JCBN Recommendations [3-7] that deal with specialized areas of carbohydrate terminology however, these documents can be consulted for further examples. Of relevance to the field, though not incorporated into the present document, are the following recommendations ... 

Carb-0. Historical development of carbohydrate nomenclature [15] 2-Carb-O.l. Early approaches... 

Not all problems were solved, however, and different usages were encountered on the two sides of the Atlantic. A joint British-American committee was therefore set up, and in 1952 it published Rules for Carbohydrate Nomenclature [18]. This work was continued, and a revised version was endorsed in 1963 by the American Chemical Society and by the Chemical Society in Britain and published [19]. The publication of this report led the IUPAC Commission on Nomenclature of Organic Chemistry to consider the preparation of a set of IUPAC Rules for Carbohydrate Nomenclature. This was done jointly with the IUPAC-IUB Commission on Biochemical Nomenclature, and resulted in the Tentative Rules for Carbohydrate Nomenclature, Part I, 1969 , published in 1971/72 in several journals [1]. It is a revision of this 1971 document that is presented here. In the present document, recommendations are designated 2-Carb-n, to distinguish them from the Carb-n recommendations in the previous publication. 

Note. In carbohydrate nomenclature, substitution at a heteroatom is normally indicated by citing the locant of the attached carbon atom, followed by a hyphen, and then the italicized heteroatom element symbol, e.g. 2-0-methyl, 5-N-acetyl. Substituents on the same kind of heteroatom are grouped (e.g. 2,3,4-tri-0-methy 1), and substituents of the same kind are cited in alphabetical order of heteroatoms (e.g. 5-N-acetyl-4,8,9-tri-0-acetyl). The alternative format with superscript numerical locants (e.g, N5,(/,(), ( -tetraacetyl), used in some other areas of natural product chemistry, is unusual in carbohydrate names. 

In his preface to Volume 8 of Advances, published in 1953, M. L. Wolfrom, the founding editor, noted that Carbohydrate nomenclature has been an everpresent problem in this series. . and drew attention to the agreement between American and British carbohydrate chemists that resulted in the published British-American Rules of Carbohydrate Nomenclature. A revision of that document was published in 1962, to be followed seven years later by an internationally proposed set of guidelines for naming carbohydrates and their derivatives. 

Since the early 1970s a panel convened by the International Union of Pure and Applied Chemistry and the International Union of Biochemistry and Molecular Biology has been working to formulate recommendations for carbohydrate nomenclature that meet developing needs of research and electronic data handling, while retaining links to the established literature base on carbohydrates. The realization of these endeavors is presented here in the final document Nomenclature of Carbohydrates, which provides a definitive reference for current researchers, both in the text version and in the version accessible on the World Wide Web (http //www.chem.qmw.ac.uk/iupac/2carb/), where amendments and revisions are maintained. 

Editor, Symposia Organizer, and Expert on Carbohydrate Nomenclature... 

The carbohydrate nomenclature jointly established by the American and British Committees4 does not specifically refer to the branched-chain sugars nevertheless, the application and extension of its Rules can provide definitive names to augment or to replace the trivial or unsystematic terms which have been conferred on naturally occurring, branched-chain sugars and related synthetic products, including the branched-chain saccharinic acids.6 9... 

Modified to conform with accepted carbohydrate nomenclature. 

Erythro/threo Terms derived from carbohydrate nomenclature used to describe the relative configuration at adjacent stereocenters. Erythro refers to a configuration with identical or similar substituents on the same side of the vertical chain in Fischer projection. Conversely, a threo isomer has these substituents on opposite sides. These terms came from the nomenclature of two carbohydrate compounds, threose and erythrose (see Fig. 1-35). 

Tentative rules for carbohydrate nomenclature. Part 1 J. Biol Chem. mi) 247, 613-634 Corrections, Eur. J. Biochem. (1972) 25, 4 Conformational nomenclature for five- and six-mem-bered ring forms of monosaccharides and their derivatives... 

In this biographical notice, we shall maintain, in English translation, some of the nomenclature employed by Emil Fischer. The names used by Fischer sufficed to meet the needs of the structures as then known, and have served as a solid basis for modem carbohydrate nomenclature, which, however, requires the definition of structural features unknown to Fischer. 

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