Carbohydrates and their derivatives

Carbohydrates are still difficult to deal with in prebiotic chemistry although the first laboratory syntheses of carbohydrates were described more than 150 years ago, their prebiotic synthesis is still unclear. 

About 40 different sugars are formed. Those required for nucleic acid synthesis, ribose and deoxyribose, are obtained in yields of less than 1%. It is completely unclear whether these could have been separated from the others under primeval Earth conditions (Shapiro, 1988). 

Ribose is relatively unstable, which leads all the critics of an RNA world to look for other models. The half-life of ribose is only 73 minutes at 373 K and pH 7, but increases at 273 K to 44 years. 

The above-mentioned facts require that ribose must have undergone further reactions immediately after its formation under prebiotic conditions. More than 20 years ago R. Shapiro (1984) pointed out the immense problems which would have needed to be solved in prebiotic nucleic acid formation. 

Larralde et al. (1995) published work on the ribose problem in the Proceedings of the National Academy of Science. They suggested that the results referred to 

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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. 

B. Interactions of [organotinllV)]" with carbohydrates and their derivatives... 

While the broad mission of the National Bureau of Standards was concerned with standard reference materials, Dr. Isbell centered the work of his laboratory on his long interest in the carbohydrates and on the use of physical methods in their characterization. Infrared spectroscopy had shown promise in providing structural and conformational information on carbohydrates and their derivatives, and Isbell invited Tipson to conduct detailed infrared studies on the extensive collection of carbohydrate samples maintained by Isbell. The series of publications that rapidly resulted furnished a basis for assigning conformations to pyranoid sugars and their derivatives. Although this work was later to be overshadowed by application of the much more powerful technique of nuclear magnetic resonance spectroscopy, the Isbell— Tipson work helped to define the molecular shapes involved and the terminology required for their description. 

B. Gyurcsik and L. Nagy, Metal complexes of carbohydrates and their derivatives Coordination equilibrium and structure, Coord. Chem. Rev., 203 (2000) 81-149. 

Despite the results obtained by Jones and coworkers,409 interest in the separation of carbohydrate acetates lapsed for several years. This was partly due to the complexity of the liquid phase used by these investigators, and partly because the acetates of certain common alditols could not be separated on the then-available column-packings. In addition, it was at just about this time that Sweeley and coworkers5 introduced the use of trimethylsilylation, and demonstrated that a wide range of carbohydrates and their derivatives could be separated by this technique. 

The study of such techniques as F.t.-i.r., computerized laser-Raman, or n.c.a., however great their degree of sophistication, should have practical utility for carbohydrate chemists and biochemists. That is why, amid the current problems elucidated by the interpretation of the vibrational spectra of carbohydrates and their derivatives, a section has been reserved for discussion of structure-properties relationships. 

Hatley, R.H.M. Blair, J.A. Stabilization and delivery of labile materials by amorphous carbohydrates and their derivatives./. Mol. Catal. B 7,11-19,1999... 

M. Fedoronko, The electrochemistry of carbohydrates and their derivatives, Adv. Carbohydr. Chem. Biochem., 29 (1974) 107—171. 

Proton magnetic resonance (p.m.r.) spectroscopy is now firmly established as the most widely used technique for the structural, configurational, and conformational analysis of carbohydrates and their derivatives. Much of the earlier work on the application of... 

The first Chapter on nuclear magnetic resonance2 in this Series was devoted principally to p.m.r. spectroscopy, because, up to 1964, virtually no magnetic resonance studies of other nuclei in carbohydrates and their derivatives had been made. The present Chapter is also concerned mainly with the p.m.r. technique, in the expectation that the broad subject of nuclei other than protons will be treated separately in this Series. 

Lewis, N.G. Davin, L.B. Sarkanen, S. In Comprehensive Natural Products Chemistry - Carbohydrates and their Derivatives including Tannins, Cellulose and Related Lignins, Barton, D.H.R. Nakanishi, K., Eds. Elsevier Science New York, 1999 Vol. 3, pp. 617-745. 

Atalla RH (1999) Celluloses. In Knto BM (ed) Carbohydrates and their derivatives including tannins, cellulose, and related lignins, vol 3, Comprehensive natural products chemistry. Elsevier, Amsterdam, chap 3.16... 

Wight TN (1999) Biosynthesis of Proteoglycans. In Pinto BM (ed) Carbohydrates and their Derivatives Including Tannins, Cellulose, and Related Lignins (Comprehensive Natural Products Chemistry), vol 3. Elsevier, Amsterdam,... 

Carbohydrate chemistry presents some special problems in nomenclature. These have been studied by a committee of the American Chemical Society s Division of Carbohydrate Chemistry in close cooperation with a British committee (3). The rules are recommended for use whenever systematic names for carbohydrates and their derivatives are required. Further work is being done by these groups. 

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