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F 2006 BIOC 3405. 11-09-06. Carbohydrates. C n (H 2 O) n primarily Mono- Oligo- Polysaccharides. Representations. Fisher projections Haworth structures More realistic structural formulae. Aldoses and Ketoses. Family of structures Most D-structures survey. Reducing Sugars.
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F 2006 BIOC 3405 11-09-06
Carbohydrates • Cn(H2O)n primarily • Mono- • Oligo- • Polysaccharides
Representations • Fisher projections • Haworth structures • More realistic structural formulae
Aldoses and Ketoses • Family of structures • Most D-structures • survey
Reducing Sugars • Aldehyde + Cu2+ Acid + Cu+ Glucose + Cu2+ gluconic acid + Cu+ Sucrose + Cu2+ no reaction
Mutarotation of glucose • Prepare pure +glucose (Say -D-glucopyranose) • Dissolve in H2O • In time, optical rotation diminishes. • Found to be a mixture (melting point lower) • What has happened? • Answer: “Mutarotation”
Naming oligos • Config of anomeric C of non-reducing monosaccharide • Name of monosaccharide, with 5 or 6 ring word (furan- or pyran-) and -osyl • Dash • Hookup, with , in parentheses • Dash • Name of reducing monosaccharide, with –ose Example: maltose -D-glucopyranosyl-(14)-D-glucopyranose
Carbon 4 is epimeric Shorthand notation
Nonreducing disaccharides • Config of anomeric carbon of either sugar • Name with furan- or pyran- of sugar and osyl ending • Dash • Linkage with arrow within parentheses • Config of other sugar’s anomeric C • Name with –oside ending Example: sucrose -D-glucopyranosyl-(12)--D-fructofuranoside
peptidoglycans glycosaminoglycans hyaluronate agarose Cellulose Glycogen Starch chitin
(14) linkage Chitin N-acetyl-D-glucopyranosamine (GlcNac)
3-D structure of polysacharrides • cf with proteins • Dihedral angles ,