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F 2006 BIOC 3405

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

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  1. F 2006 BIOC 3405 11-09-06

  2. Carbohydrates • Cn(H2O)n primarily • Mono- • Oligo- • Polysaccharides

  3. Representations • Fisher projections • Haworth structures • More realistic structural formulae

  4. Aldoses and Ketoses • Family of structures • Most D-structures • survey

  5. Reducing Sugars • Aldehyde + Cu2+ Acid + Cu+ Glucose + Cu2+ gluconic acid + Cu+ Sucrose + Cu2+  no reaction

  6. 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”

  7. A glycoside

  8. 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-(14)-D-glucopyranose

  9. Carbon 4 is epimeric Shorthand notation

  10. 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-(12)--D-fructofuranoside

  11. Found in hemolymph

  12. polysaccharides

  13. peptidoglycans glycosaminoglycans hyaluronate agarose Cellulose Glycogen Starch chitin

  14. amylopectin

  15. cellulose

  16. Note extension in two dimensions

  17. Fungus contains cellulase

  18. (14) linkage Chitin N-acetyl-D-glucopyranosamine (GlcNac)

  19. Chitin

  20. 3-D structure of polysacharrides • cf with proteins • Dihedral angles ,

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