IUPAC carbohydrate

The formal lUPAC rules for a and 3 notation in carbohydrates are more detailed and less easily understood than most purposes require. These rules can be accessed at http //www.chem.qmw.ac. uk/iupac/2carb/06n07.html. 

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 ... 

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. 

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. 

IUPAC-IUBMB Joint Commission on Biochemical Nomenclature (JCBN), Nomenclature of carbohydrates (Recommendations 1996), http //www.chem.qmul.ac.uk/iupac/2carb/. 

V. Jager, R. Muller, T. Leibold, U. Stahl, J. Raczko, B. Steuer, P. Poggendorf, and T. Gracza, Abstr. Papers XVIth Int. Carbohydr. Symp. IUPAC, Paris, July 5-10, 1992, IL-A9. 

The two stereoisomeric furanose forms of D-erythrose are named a-D-erythro-furanose and 3-D-erythrofuranose. The prefixes a and p describe the relative configuration of the anomeric carbon. The configuration of the anomeric carbon is compared with that of the highest numbered chirality center in the molecule—the one that determines whether the carbohydrate is d or l. Chemists use a simplified, informal version of the IUPAC rules for assigning a and p that holds for carbohydrates up to and including hexoses. 

Nomenclature of Carbohydrates http //www.chcm.qinul.ac.Lik/iupac/2carb/ Nomenclature of Carotenoids http //www.chcin.qmul.ac.uk/iiipac/carot/ Nomenclature and Symbols for Folic Acid and Related Compounds http //www. chem.qmul.ac.uk/iupac/misc/folic.html... 

The saccharides have long and awkward names by the IUPAC system, consequently a highly specialized nomenclature system has been developed for carbohydrates. Because this system (and those like it for other natural products) is unlikely to be replaced by more systematic names, you will find it necessary to memorize some names and structures. It will help you to remember the meaning of names such as aldopentose and ketohexose, and to learn the names and details of the structures of glucose, fructose, and ribose. For the rest of the carbohydrates, the nonspecialist needs only to remember the kind of compounds that they are. 

The Binding of Carbohydrate Structures with Antibodies and Lectins, R. U. Lemieux, Proc. of the 28th IUPAC Congress, Vancouver, Canada, 16-22 August 1981. In Frontiers in Chemistry, K. J. Laidler (Ed) Pergamon Press, Oxford (1981) pp. 3 26. 

Nomenclature of carbohydrates (IUPAC-IUBMB Recommendations 1996), Carbohydr. Res., 297 (1997) 1-92 see Rule 2-Carb-26. 

Table I, which lists a number of mono-, oligo-, and polysaccharides and derivatives whose motional descriptions are available based on qualitative arguments, summarizes the experimental conditions and types of measurements used to obtain those descriptions. Table II deals specifically with those carbohydrates for which a quantitative treatment and dynamic modeling have been undertaken. In naming the compounds listed in Tables I and II, IUPAC rules are used for monosaccharide and less complex oligosaccharide molecules. However, empirical names are used for unusual oligosaccharides involving a complex aglycon substituent and polysaccharides. The gross motional features of a number of the compounds in Table I have been discussed in references 6-8, and will be mentioned here only if necessary for further clarification or for comparison with quantitative results.

It should be noted that the numbering of the atoms in the IUPAC nomenclature differs from that in the nomenclature used in carbohydrate chemistry, which sometimes leads to confusion. The present article follows the IUPAC nomenclature, except for the compound with carbohydrate sources. 

Although the IUPAC nomenclature is recommended in the majority of journals, it can be seen clearly that the use of jargon in respect to crown ethers and cryptands enjoys a great popularity. Not surprisingly, since their exact and complicated IUPAC names are difficult to mention frequently in the text. Common abbreviations can be found almost in all review articles 2), however, for the convenience sake, we draw attention to some of them to which is referred here. Chart 1 depicts simple examples of N,N -dimethyl diazacoronands, cryptands and more elaborated cryptands incorporating carbohydrate units. The abbreviations below each formula are easy to follow. 

Although the IUPAC has dropped the term ketal for the acetal of a ketone, most carbohydrate chemists still use the term. Therefore, the cyclic hemiacetal of fructose is often called a hemiketal. 

IUPAC-IUB Commission on Biochemical Nomenclature, 202, 258(4) IUPAC-1UBMB Nomenclature of Carbohydrates, 144, 195(lb)... 

Polysaccharides are formed by glycosidically linked carbohydrate (glycosyl) residues. As expected, the nomenclature of polysaccharides is based on the nomenclature of carbohydrates. The recommendations of the International Union of Pure and Applied Chemistry-International Union of Biochemistry and Molecular Biology Joint Commission on Biochemical Nomenclature (lUPAC-IUB JCBN) have been pub-lished and are open to the public at http //www. chem.qmul.ac.uk/iupac/2carb/39.html. 

Dn + An, etc.) recommended by IUPAC, which, though, for important reactions is given in a foortnote. The Jencks-Guthrie system is in my view superior, as it can indicate preassociation reactions and proton transfers, which are particularly important in carbohydrate chemistry, in a way that the older Ingold system cannot, but unfortunately in the 15 years since its formulation, the Jencks-Guthrie system has not found widespread acceptance. 

IUPAC-IUBMB Nomenclature of Carbohydrates,1"Adv. Carbohydr. Chem. Biochem., 52 (1997) 43-177 see also Nomenclature of Cyclitols, Eur. J. Biochem., 57 (1975) 1-7. 

Volume 52 of this series featured the comprehensive IUPAC-IUBMB document Nomenclature of Carbohydrates that meets a long-standing need for up-to-date standardized nomenclature for sugar derivatives and complex saccharides. Ongoing work of the international committee has... 

Whereas organization and use of Part II Report are unchanged, clearly the subject of nomenclature is one of a state of flux. By the end of 1980, many of the draft documents of the lUB-IUPAC Joint Commission on Biochemical Nomenclature relating to carbohydrates should have been finalized. At that... 

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