Carbohydrates photochemistry

The purpose of the present article is to review comprehensively those photochemical reactions of carbohydrates for which product structures have been established, and to apply current mechanistic reasoning to the understanding of these reactions. Two reviews of carbohydrate photochemistry already exist. The first1 2 was published in this Series in 1963, prior to the considerable recent growth in this field, and the second was a brief summary published in the Japanese literature in 1973. 

Irradiation of unprotected carbohydrates was the subject of greatest photochemical interest to the early carbohydrate photochemists.1 The investigations of these early workers were concerned primarily with the effect of reaction conditions upon the photochemical process, rather than with the identity of the reaction products. Between 1960 and 1969, a comprehensive series of papers was published on the photochemical reactions of D-glucose and D-glucitol.95-99 These studies contributed greatly to understanding of the photochemistry of unprotected carbohydrates, as not only was the result of variation in the reaction conditions studied but also the structures of the products were determined. 

Phenol-carbohydrate derivatives, in higher plants, 20, 371-408 Photochemistry, of carbohydrates, 18, 9-59 Physical chemistry, of carbohydrates, 15, 11-51 of starch, 11, 335-385 Physical properties, of solutions of polysaccharides, 18, 357-398... 

Advances in Carbocation Chemistry Advances in Carbohydrate Chemistry and Biochemistry Advances in Catalysis Advances in Cydoaddition Advances in Free Radical Chemistry Advances in Heterocyclic Chemistry Advances in Metal-Organic Chemistry Advances in Molecular Modeling Advances in Organometallic Chemistry Advances in Oxygenated Processes Advances in Photochemistry Advances in Physical Organic Chemistry Advances in Protein Chemistry Advances in Theoretically Interesting Molecules... 

Because the number of papers in chemistry has become so large, the Royal Society of Chemistry publishes annual-review-type volumes of smaller scope, called Specialist Periodical Reports. Among those of interest to organic chemists are Carbohydrate Chemistry (vol. 22 covers 1988) Photochemistry" (vol. 21 covers 1988-1989) and General and Synthetic Methods, (vol. 12 covers 1987). 

In recent years, the introduction of modern instrumentation has changed the orientation of research in the photochemistry of carbohydrates. After the first studies of the physical properties of irradiated reaction mixtures, identification of photopro-tation of research in the photochemistry of carbohydrates. After the first studies of the physical properties of irradiated reaction mixtures, identification of photoproducts was then undertaken and finally, an increasing use of free radical reactions including photochemical ones was applied to the synthesis of complex organic ads. 

With increasing theoretical and practical knowledge in photochemistry, synthetic applications of photochemical reactions to carbohydrates are a powerful tool for further research. 

P. M. Collins and F. Famia, The photochemistry of ketones derived from carbohydrates. Part 10. A study of stereochemical influences on photo-induced rearrangements and ring expansions of 3-oxacyclopentanones using l,2-0-isopropylidenefuranos-3-ulose derivatives, J. Chem. Soc. Perkin. Trans. 1, (1985) 575-581. 

Type II photocyclizations of carbohydrates. Journal of Photochemistry and Photobiology, A Chemistry, 62, 241-244. 

Perlin, A. S., Action of Lead Tetraacetate on the Sugars, 14, 9-61 PERLIN, A. S., [Obituary of] Clifford Burrough Purves, 23, 1-10 Phillips, G. O., Photochemistry of Carbohydrates, 18, 9-59 PHILLIPS, G. O., Radiation Chemistry of Carbohydrates, 16, 13-58 Pigman, Ward, and Isbell, Horace S., Mutarotation of Sugars in Solution Part I. History, Basic Kinetics, and... 

Ando has published a monograph dealing with the synthetic uses of ketone and alkene photochemistry. A review by Overend has focused attention on the synthesis of novel carbohydrates, including applications of photochemical methods. Other reviews have examined the developing area of photochemical asymmetric synthesis. Rau has reviewed asymmetric photochemistry in solution. 

Activation for chemical transformations can be accomplished by different methods, traditionally by heating the reaction vessel with an oil bath. Other methods are used for shorter periods, e.g. heating by microwave irradiation or ultrasound treatment. Another possibility is irradiation by electromagnetic radiation in the visible and UV region of the spectrum, which is referred to as photochemistry. This kind of activation is used in nature for building up carbohydrates by photosynthesis. 

Photochemistry Mass Spectrometry Carbohydrate Chemistry Amino-acids, Peptides, and Proteins The Alkaloids Terpenoids and Steroids Organophosphorus Chemistry... 

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