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F 2006 BIOC 3405

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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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Presentation Transcript
carbohydrates
Carbohydrates
  • Cn(H2O)n primarily
  • Mono-
  • Oligo-
  • Polysaccharides
representations
Representations
  • Fisher projections
  • Haworth structures
  • More realistic structural formulae
aldoses and ketoses
Aldoses and Ketoses
  • Family of structures
  • Most D-structures
    • survey
reducing sugars
Reducing Sugars
  • Aldehyde + Cu2+ Acid + Cu+

Glucose + Cu2+ gluconic acid + Cu+

Sucrose + Cu2+  no reaction

mutarotation of glucose
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
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

slide21

Carbon 4 is epimeric

Shorthand notation

nonreducing disaccharides
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

slide27

peptidoglycans

glycosaminoglycans

hyaluronate

agarose

Cellulose

Glycogen

Starch

chitin

slide36

(14) linkage

Chitin

N-acetyl-D-glucopyranosamine

(GlcNac)

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