215F07-notes-11-9-07-carbsa

215F07-notes-11-9-07-carbsa - 11/02/2007 07:01 PM 2-Carb-6...

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Unformatted text preview: 11/02/2007 07:01 PM 2-Carb-6 and 2-Carb-7 Page 1 of 8 http://www.chem.qmul.ac.uk/iupac/2carb/06n07.html Nomenclature of Carbohydrates (Recommendations 1996) 2-Carb-6 and 2-Carb7 Continued from 2-Carb-5 Contents 2-Carb-6. Anomeric forms; use of and 6.1. The anomeric centre 6.2. The anomeric reference atom and the anomeric configurational symbol 6.3. Mixtures of anomers 6.4. Use of and 2-Carb-7. Conformation of cyclic forms 7.1. The conformational descriptor 7.2. Notation of ring shape 7.3. Notation of variants 7.4. Enantiomers References for this section 2-Carb-6 Anomeric forms; use of and 2-Carb-6.1. The anomeric centre The new centre of chirality generated by hemiacetal ring closure is called the anomeric centre. The two stereoisomers are referred to as anomers, designated or according to the configurational relationship between the anomeric centre and a specified anomeric reference atom. 2-Carb-6.2. The anomeric reference atom and the anomeric configurational symbol ( or ) The anomeric reference atom is the configurational atom (see 2-Carb-4.2 and 2-Carb-4.3 ) of the parent, unless multiple configurational prefixes (see 2-Carb-8.3 ) are used. If multiple configurational prefixes are used, the anomeric reference atom is the highest-numbered atom of the group of chiral centres next to the anomeric centre that is involved in the heterocyclic ring and specified by a single configurational prefix. In the anomer, the exocyclic oxygen atom at the anomeric centre is formally cis , in the Fischer projection, to the oxygen attached to the anomeric reference atom; in the anomer these oxygen atoms are formally trans. The anomeric symbol or , followed by a hyphen, is placed immediately before the configurational symbol D or L of the trivial name or of the configurational prefix denoting the group of chiral carbon atoms that includes the anomeric reference atom. Examples: 11/02/2007 07:01 PM 2-Carb-6 and 2-Carb-7 Page 2 of 8 http://www.chem.qmul.ac.uk/iupac/2carb/06n07.html - D- gluco - D-Glucopyranose - D- gluco - D-Glucopyranose - L- arabino Methyl - L-arabinopyranoside - L- threo Methyl - L-threofuranoside 11/02/2007 07:01 PM 2-Carb-6 and 2-Carb-7 Page 3 of 8 http://www.chem.qmul.ac.uk/iupac/2carb/06n07.html - D- galacto Methyl - D-galactofuranoside L- glycero- - D- manno Methyl L- glycero- - D- manno-heptopyranoside - D- arabino Methyl - D-fructofuranoside D- glycero- - D- galacto Methyl 5-acetamido-3,5-dideoxy- D- glycero- - D- galacto-non-2-ulopyranosonate (see 2-Carb-14.22-Carb-14....
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This note was uploaded on 04/01/2008 for the course CHEM 215 taught by Professor Koreeda during the Fall '07 term at University of Michigan.

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215F07-notes-11-9-07-carbsa - 11/02/2007 07:01 PM 2-Carb-6...

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