En Block Approach of Structure Elucidation of Linear Isomeric Aldohexoses as Related to Aldaric (Saccharic) Acids

Dumitru Petru IGA

Abstract


Structure elucidation of the 16 isomeric linear aldohexoses is approached en block, in a clear, logic, concise, coherent, manner. The main premise, or paradigm, of this paper is structure elucidation of (+)-tartaric acid by Bijvoet. Other premise is a preparative method elaborated by Baer and Fischer, whose instructive potential is disclosed for the first time in this paper. It concerns elucidation of configuration of C-2 by using di-O-isopropylidenic derivatives of hexitols.

 

 


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Levy, D. E., & Fügedi, P., (eds.) (2006). The Organic Chemistry of Sugars, CRC Press, Taylor & Francis Group, London.

IUPAC-IUBMB Joint Commission on Biochemical Nomenclature (JCBN) (1997). Nomenclature of Carbohydrates. Recommendations 1996. Eur. J. Biochem. 243, pp. 9.

Schmidt, R. R. (1986). Neue Methoden zur Glycosid- und Saccharidsynthese - Gibt es Alternativen zur Koenigs-Knorr-Methode? Angew. Chem. 98, pp. 213-236.

Iga, D. P. & Iga, S. (1993). A Mathematical Formula for the Evaluation of Ganglioside Polymorphism. Rev. Roum. Biochim. 30, pp. 21-22.

Laine, R. A. (1994). Invited Commentary: A calculation of all possible oligosaccharide isomers both branched and linear yields 1.05 × 1012 structures for a reducing hexasaccharide: the Isomer Barrier to development of single-method saccharide sequencing or synthesis systems. Glycobiology 4, pp. 759-767.

Gamow, G. (1954). Possible relation between deoxyribonucleic acid and protein structure. Nature 173, pp. 318.

Alexuru, G. I., & Iga, D. P., A Multiple Bridge between Mathematics, Genetics, Chemistry and Linguistics. Seventh Conference of the International History, Philosophy and Science Teaching, Winnipeg, Canada, July 30-August 3, 2003, pp. 20-23.

Homer „The Iliad” (1991). Translated by Robert Fagles, Penguin Books, New York, Book 2, Verses 147- 152.

Fittig, R. (1871). Ueber die Constitution der sogenannten Kohlenhydrate, L. F. Fues, Tübingen.

Kiliani, H. (1885). Ueber das Cyanhydrin der Lävulose. Ber. deut. chem. Ges. 18, pp. 3066-3072.

Kiliani, H. (1886). Ueber Arabinose. Ber. deut. chem. Ges. 19, pp. 3029-3036.

Lichtenthaler, F. W. (1992). Emil Fischer’s establishment of the configuration of the sugars: a centennial tribute. Angew. Chem. Int. Ed. 31, pp. 1541-1556.

van’t Hoff, J. H. (1877). Die Lagerung der Atome im Raume, Vieweg. Braunschweig.

Le Bel, J. A. (1874). Sur les relations qui existent entre les formules atomiques des corps organiques et le pouvoir rotatoire de leurs dissolutions. Bull. soc. chim. 22, pp. 337-347.

Fischer, E. (1891). Ueber die Configuration des Traubenzuckers und seiner Isomeren. Ber. deut. chem. Ges. 24, pp. 1836-1845.

Fischer, E. (1891). Ueber die Configuration des Traubenzuckers und seiner Isomeren. II. Ber. deut. chem. Ges. 24, pp. 2683-2687.

Kuroda, R., Endo, B., Abe, M., & Shimizu, M. (2009). Chiral blastomere arrangement dictates zygotic left-right asymmetry pathway in snails. Nature 462, pp. 790-794.

Vermeij, G. J. (1975). Evolution and distribution of left-handed and planispiral coiling in snails. Nature 254, pp. 419-420.

Malus, E. L. (1809). Sur une propriété de la luminère réfléchie. Mém. Soc. Arcueil 2, pp. 143-158.

Arago, F. J. D. (1811). Mémoire sur une modifaction remarquable qu’éprouvent les rayons lumineux dans leur passage à travers certains corps diaphanes d’optique. Mém. l’Inst. 12, pp. 93-134.

Biot, J. B. (1815). Phènoménes de polarisation successive observés dans la fluides homogènes. Soc. philom. Bull. pp. 190-192.

Fischer, E. (1891). Ueber d. und i. Mannozuckersäure. Ber. deut. chem. Ges. 24, 539-546.

Tilden, W. A. (1921). Famous Chemists, The Men and their Work, George Routledge & Sons, London.

Kendall, J. (1953). Great Discoveries by young chemists, Th. Y. Growell Company, New York.

Nicol, W. (1829). On a Method of So Far Increasing the Divergency of the Two Rays in Calcareous Spar That Only One Image May Be Seen at a Time. Edinburgh New. Phil. J. 6, pp. 83-84.

Pasteur, L. (1848). Memoire sur la relation qui peut exister entre la forme cristalline et la composition chimique, et sur la cause de la polarisation rotatoire. Compt. rend. 26, pp. 535-538.

Hilditch, T. P. (1911). A Concise History of Chemistry, New York, D. Van Nostrand Company.

Bijvoet, J. M., Peerdemann, A. F., & van Bommel, A. J. (1951). Determination of the absolute configuration of optically active compounds by means of X-rays. Nature 168, pp. 271-272.

Fischer, E. (1896). Configuration der Weinsäure. Ber. deut. chem. Ges. 29, pp. 1377-1383.

Malaprade, L. (1928). Oxidation of some polyalcohols by periodic acid – applications. Compt. Rend. 186, pp. 382-384.

Malaprade, L. (1928). Actions of polyalcohols on periodic acid. Analytical applications. Bull. Soc. Chim. France 43, pp. 683-696.

Jäger, V., & Wehner, V. (1989). 2-O-Benzylglyceraldehyde: a synthetic building block available in both enantiomeric forms and configurationally stable owing to rapid oligomerization. Angew. Chem. Int. Ed. Engl. 28, pp. 469-470.

Wohl, A. (1893). Abbau des Traubenzuckers. Ber. deut. chem. Ges. 26, pp. 730-744.

Ruff, O. (1898). Ueber die Verwandlung der d-Gluconsäure in d-Arabinose. Ber. deut. chem. Ges. 31, pp. 1573-1577.

Baer, E., & Fischer, H. O. L. (1939). Studies on Acetone-Glyceraldehyde. VII. Preparation of L-Glyceraldehyde and L(-) Acetone Glycerol. J. Am. Chem. Soc. 61, pp. 761-765.

Baer, E., & Fischer, H. O. L. (1939). Studies on acetone-glyceraldehyde. IV. Preparation of D-(+)-acetone glycerol. J. Biol. Chem. 128, pp. 463-473.

Schmid, C. R., Bryant, J. D., Dowlatzedah, M., Phillips, J. L., Prather, D. E., Schantz, R. D., Sear, N. L., & Vianco, C. S. (1991). Synthesis of 2,3-O-isopropylidene-D-glyceraldehyde in high chemical and optical purity: observations on the development of a practical bulk process. J. Org. Chem. 56, pp. 4056-4058.

Chittenden, G. J. F. (1982). Some aspects of the isopropylidenation of d-glucitol under neutral conditions. Carbohydr. Res. 108, pp. 81-87.

Ekeberg, D., Morgenlie, S., & Stenstrøm, Y. (2001). Synthesis of 3-hexuloses from 1,2:5,6-di-O-isopropylidenehexitols. Carbohydr. Res. 335, pp. 141-146.


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