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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F 2006 BIOC 3405

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F 2006 bioc 3405

F 2006 BIOC 3405

11-09-06


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”


F 2006 bioc 3405

A glycoside


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


F 2006 bioc 3405

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


F 2006 bioc 3405

Found in hemolymph


Polysaccharides

polysaccharides


F 2006 bioc 3405

peptidoglycans

glycosaminoglycans

hyaluronate

agarose

Cellulose

Glycogen

Starch

chitin


F 2006 bioc 3405

amylopectin


F 2006 bioc 3405

cellulose


F 2006 bioc 3405

Note extension in two dimensions


F 2006 bioc 3405

Fungus contains cellulase


F 2006 bioc 3405

(14) linkage

Chitin

N-acetyl-D-glucopyranosamine

(GlcNac)


F 2006 bioc 3405

Chitin


3 d structure of polysacharrides

3-D structure of polysacharrides

  • cf with proteins

    • Dihedral angles ,


F 2006 bioc 3405

Bacterial Lipopolysaccharide


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