Trivial names, synonyms, and also Chemical Abstracts ... pKa values are given for acids and bases, spectrophotometric data for some chromophore-containing.
c 2006 Institute of Chemistry, Slovak Academy of Sciences DOI: 10.2478/s11696-006-0030-z
BOOK REVIEWS
Dictionary of Carbohydrates. Edited by P. M. Collins. Second Edition. Chapman & Hall/CRC, Taylor & Francis Group, Boca Raton, London, New York, 2006. Pp. 1282. Price 255.- $.
The reviewed book is the second, extended edition of the important source of data for not only carbohydrate chemists but for all those active in the area of glycoscience or glycobiology. The second edition of the Dictionary is actually another proof of the fast progress and development in the field connected with the recognition of important roles of carbohydrates in living systems, in addition to their structural, nutritional, and immunochemical functions. Carbohydrates themselves or in combination with other molecules appear as molecules providing communication and signaling between the cells and organelles. The book starts with a short Table of Contents indicating the following parts: Preface, Editorial Board, Introduction, and Dictionary Entries presented in alphabetical order. The last entries, beginning with the letter “z”, are followed by two types of indexes: Name Index and Type of Compound Index. The Preface written by the main book editor, P. M. Collins, explains the differences between the first and the second edition. The second edition is an extended version by about 4000 new entries, bringing their number to about 24000. The second edition is published together with a CD-ROM version which is so important that it requires a special coverage. The Introduction provides information on what is actually covered in the book, which types of carbohydrates and their derivatives are described and how the material is organized. An example of the presentation of compounds is shown and explained in detail. The Introduction also gives the procedures how to locate compounds, which types of their names to use during the search. Trivial names, synonyms, and also Chemical Abstracts Service and IUPAC nomenclature names should be tried. In case they are not found easily in the Dictionary, it is always possible to find them in the two types of indexes at the end of the book. The Introduction also contains two double-column pages with the used Database Abbreviations and the description of the CD-ROM version of the Dictionary attached to the book. The first compound of the Dictionary is “acaciabiuronic acid”, treated slightly more than on one of the three separate columns of a page. The trivial name of the compound is followed with its official name, 6-O-βD-glucopyranuronosyl-D-galactose, and then with its Chemical Abstracts Service Registry Number, structural formula with the description of the ring and the anomeric form. This is generally the way how all the 24000 different compounds are presented. The system is the same as in the first edition. The Haworth projection formulas are the most frequent, however, in some cases where stereochemistry should be emphasized, the compounds are depicted using Fischer projections or penta- and hexagonal projections with spatial orientation of linkages pointing below and above the sheet plane. In such cases usually other stereoisomers of the compound are included. Further data about the entry include molecular formula, molecular mass, information on occurrence and physicochemical constants, such as melting point and optical rotation. Derivatives of the main entries and useful references complete the entry. To collect and organize such an enormous amount of data deserves our admiration. The amount of information compiled in the book is also documented by its weight that is almost 2 kg. The categories of compounds covered in the book are the following: 1. The parent monosaccharides and their important derivatives (all aldoses and ketoses are listed). 2. Modified monosaccharides, mainly oxidized derivatives and sugar analogues. 3. Disaccharides. 4. Tri-, oligo-, and polysaccharides. 5. Alditols and cyclitols. 6. Nucleosides. 7. Glycoside antibiotics and related compounds. 8. Other glycosides. Entries are supplied by a wide range of derivatives as subtitles, biochemical significance, eventually by information on their industrial usage. pKa values are given for acids and bases, spectrophotometric data for some chromophore-containing sugar derivatives, and toxicity data in the case of hazardous compounds. Orientation in the Dictionary is facilitated by two types of indexes at the end of the book. The Name Index is a strict alphabetical order of carbohydrates and their derivatives mentioned in the book with the reference to the page of their occurrence. The second index is the Type of Compound Index replacing the Molecular Formula Index of the first edition of the book. The Type of Compound Index is certainly more convenient for search because it does not require the calculation of the molecular formulas. In the new index the carbohydrates and their derivatives are listed alphabetically, but in smaller groups, created according to the number of carbons and arrangement of the hydroxyl groups around the pyranoid or furanoid rings. Shorter aldoses
Chem. Pap. 60 (2) 169—170 (2006) c 2006 Institute of Chemistry, Slovak Academy of Sciences
Unauthenticated Download Date | 9/24/15 11:15 PM
169
BOOK REVIEWS
are followed by longer aldoses, then aldoses are followed by ketoses, ketoses by anhydrosugars, halogenosugars, glycosylamines, aminosugars, azidosugars, thiosugars, deoxysugars (2-deoxy-, 3-deoxy-, 4-deoxy-, 5-deoxy, and 6-deoxy- and dideoxysugars are sub-grouped separately), sugar alcohols, sugar acids, etc. A separate list is devoted to reducing disaccharides, non-reducing disaccharides, trisaccharides, linear oligosaccharides, cyclic oligosaccharides, polysaccharides, carbohydrate antibiotics, and nucleosides. I believe this list is sufficient enough to assure the reader that the Dictionary covers almost all known carbohydrates and their derivatives. I checked in the Type of Compound Index the cyclic tetramer of D-glucose which I described in 1994 with G. L. Côté, the so-called cycloalternan. To my satisfaction, the compound is also included under the name “cyclo[(1→6)-αD-glucopyranosyl-(1→3)-α-D-glucopyranosyl-(1→6)-α-D-glucopyranosyl-(1→3)-α-D-glucopyranosyl-(1→)]” and the entry also refers to our original publication. The compound does not appear in the first edition of the book. Briefly about the CD-ROM version of the book. Similar to the printed book, the CD contains a manual (file CRCcarb.pdf) for installation of the software as well as for work with the installed programme. The search in the text, numerical and structure indexes offers additional possibilities according to other types of keywords and fields that were precluded by space limitations of the hard-copy version of the Dictionary. The search procedure is described in the Introduction of the hard-copy version of the book as well as in the manual. Important information is that the search can be based on combination of four of 33 different criteria, even avoiding the chemical name of compounds. There are other benefits of the CD-ROM compared to the book. The structural formula of the main entry compound, called Entry Diagram, can be copied as a picture to any of the Office or graphic programs, which means that it cannot be modified or edited as a structure. The modification can be done when the Entry Diagram is copied into the ChemOffice application, e.g. into ChemDraw Ultra. This is a great time-saver feature for all those who need to draw formulas of carbohydrate molecules. Another possibility of keeping the formulas in an editable format is their export to Structure Drawing application. The advantage of this option is that all formulas could be saved, not only the entry compound formulas. The application could be started manually without running the search. A slight disadvantage of the Structure Drawing is that the formulas are exported in a form disregarding the orientation of the bonds around the carbohydrate ring. As given above, the Dictionary of Carbohydrates is a rich source of key information for all those working in glycoscience and glycobiology. Therefore, it should become an indispensable volume in libraries of all institutions and laboratories dedicated to carbohydrates and glycoconjugates, an important “carbohydrate bible”. P. Biely
170
Unauthenticated Download Date | 9/24/15 11:15 PM
Chem. Pap. 60 (2) 169—170 (2006)
