Names:

 

 

 

 

 

 

 

 

 

 

 

The definition of a sugar

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

A 6-member heterocyclic ring containing oxygen and two double bonds within the ring.

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

The name for this structures suggests segregation
wpe1.gif (1545 bytes)

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

The name of this structure suggests symmetry
wpe2.gif (1515 bytes)

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

The name of the simplest ketose

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

CHEMISTRY

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

This reaction is typical of aldehydes and nucleophiles

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

This adds to a hemiacetal to form an acetal.

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

The disaccharide sucrose, Glc  α(1--> 2) Frc can not do this, but the disaccharide lactose, Gal β(1 --> 4) Glc can.
wpeF.gif (5758 bytes)

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

This reagent and catalyst can be used to cleave acetal links

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

amide: peptide bond :: acetal: ______

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

ISOMERS

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

The only aldose with all bulky substituents in the equatorial position
wpe5.gif (1649 bytes)

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

This pair represents a certain kind of configurational isomers
wpeD.gif (2542 bytes)

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

This pair represents a certain kind of configurational isomers.
wpeE.gif (2516 bytes)

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

The penultimate  C (and last chiral C) contains an OH that points to the right in this kind of sugar.

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

These two different types of conformers of aldoses are clearly different from configuration isomers.

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

PROJECTIONS

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

The dominant form of Glc in solution

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

The dominate form of Glc in a polysaccharide

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

The dominant form of fructose in solution

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

This is the simplest 3C aldose
wpe3.gif (1220 bytes)

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

The direction that an -OH group points in a Haworth projection if it points to the right in the aldose or ketose linear form

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

DERIVATIVES

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

This sugar contains a phosphate group, which are common in sugar derivatives as they undergo catabolic degradation in cells.
wpeB.gif (2102 bytes)

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

This sugar is in ATP
wpe6.gif (2352 bytes)

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

The name of this sugar implies that it is a sugar-amine derivative
wpeA.gif (2127 bytes)

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

The name of this sugar derivative implies that it is an acid.
wpe9.gif (1694 bytes)

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

This structure, derived from D-ManNAc and pyruvic acid, might prove to be the one which most separates human and chimps.
wpe8.gif (3626 bytes)

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

POLYSACCHARIDES

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

This polysaccharide is used for energy storage in plants

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

This polysaccharide is used for energy storage in animals.

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

This polysaccharide is the major constituents of exoskeletons.

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

This link glycosidic link is found in glycogen and starch

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

This glycosidic link is found in cellulose.

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

GAG'S

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

This is the number of monosaccharides in the repeat unit of glycosoaminoglycans.

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

This carboxylic acid derivative of glucose is fond in heparin and chondrotin sulfate.

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

This glycosidic link connects monomers in the dissacharide repeat of heparin.

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

This glycosoaminoglycan is found in synovial fluid

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

This is the net charge at physiological pH on the repeat dissacharide unit of heparin.

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

CELL WALL

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

Found in bacteria, these structures contain both carbohydrate and amino acids.

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

Bacteria cell walls contain a repeat of this dissacharide unit.

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

The  link between  NAM (MurNAc) on adjacent strands of a bacterial cell wall contains a pentapeptide of this amino acid. 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

Attached to NAN in Gram + bacterial cell walls, teichoic acid consists of a polymer of this molecule linked by phosphodiester bonds.

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

The names of two unusual amino acids found in bacterial cell walls. 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

GLYCOPROTEINS

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

N-linked oligosaccharides usually connect to a protein at this amino acid.

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

O-linked oligosaccharides usually connect to a protein at this amino acid.

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

This sugar is found in all high mannose, N-linked oligosaccharides in glycoproteins.

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

Complex N-linked oligosaccharides in glycoproteins usually terminate in this sugar derivatives.

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

This structure is usually found in these types of N-linked oligosaccharides
wpe1.gif (4271 bytes)

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

PROTEOGLYCANS AND MEMBRANES

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

This kind of glycoprotein has an extensive amount of glycosoaminoglycan covalently attached to a protein core.

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

These two sites are where you would expect to find proteoglycans.

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

Water-soluble proteins can be attached to membranes by attaching a isoprenoid derivative to this amino acid.

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

The phospholipid is often attached to GlcNAc in soluble glycoproteins and anchors them to membranes.

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

Of a eukaryotic, Gram (+) bacteria, or Gram (-) bacteria, the one with the most complicated membrane/cell wall structure.

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

FINAL JEOPARDY

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

THIS IS FINAL JEOPARDY!

 

This structural feature of complex carbohydrates explains why structural determination and synthetic methods to make them have been only recently developed. 

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