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35 Cards in this Set

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Nomenclature
Carbohydrates are hydrates of carbon
monosacc: are simplest form
oligo: 2-10 monos
polysacc: polymers of simple sugars
Monosaccharides
tri/tetr/pent-ose denote C#
aldoses with 3> or ketoses with 4> C's are chiral
aldose

ketose
glyceraldehyde: H-C=O

dihydroxyacetone: C=O
Stereochemistry with D and L
Refers to configuration of the highest-#ed asymmetric center
D-sugars are predominate
purpose of D and L configurations
Galactosemia: failure to convert galactose to glucose results in accumulation of Gal in blood stream which causes cirrhosis and retardation
enantiomers of mirror image configurations
only in the middle of molecule switching the OH and H attached to parent C strand
aldopentoses
ribose, xylose
aldohexoses
glucose, galactose, mannose
ketopentoses
ribulose, xylulose
ketohexoses
fructose
Cyclic monosacc and anomeric forms
(alcohol)
glu, fru, aldohex, ketohex
glu:(aldose) hemiacetal
fru:(ketose)hemiketal
aldohex: form pyranose
ketohex: form furanose
Haworth projections
draws sugars, represent pyranose and furanose as hex and pent rings perpendicular to the plane of the paper.
Fischer to haworth
left:above ring
right:below ring
Haworth alpha:OH below ring(both for D)beta:OH above ring
beta-D-fructofuranose
linear form of D-fructose undergoes intramolecular rxn to from a cyclic hemiketal.
C5-OH attacks C2=O
anomers
cyclization of sugars creates one more chiral center that is the anomeric C, conversion of C=O to C-OH
anomeric C continued
OH group in the anomeric C may be alpha or beta
For D-sugars, alpha has OH down and beta's is up
Chair and boat conformations
chair is 109 degrees
equatorial: coplanar with ring
axial: parallel to axis
rules of chair and boat
chair are more stable
bulky R groups on rings most likely fill equatorial positions
Monosaccharide derivitives
(reducing sugars)
glucose is one, basis for diagnostic tests for blood sugar
sugars with free anomeric C's:will reduce oxidizing agents like peroxide.The redox rxns convert sugar to acid
More derivitives:
sugar alcohols
deoxy sugars
sugar esters
alc: mild reduction
deoxy: DNA constituents
amino: amino instead of OH
sugar alcohols
linear, dont cyclize, sweet
deoxy sugars
one or more OH replaced by H
occur in glycoproteins
sugar esters
metabolic intermediate
complete P and O, R group
amino sugars
amino instead of OH at C2
oligosacc and polysacc
Beta-D-glucosamine
Beta-D-galactosamine
glu:H up
gal:H down
both have NH2 parallel to O
ketal to hemiketal
(both reversible)
Acetal to hemiacetal
4R groups + H2O--> 3R + R-OH

3R + H2O--> 2R + R-OH
Oligosaccharides

OH above=beta (visa versa)
HOH:free anomeric C (reducing end)
sucrose is NOT a reducing sugar
alpha 1,4: glycosidic is bent
beta 1,4: straight/stretched
Common disaccharides
lac: gal-B-1,4-Glc....milk
su: Glc-A-1,2-Fru....plants
malt:Glc-A-1,4-Glc
celluobiose: Glc-B-1,4-Glc
Polysacchardides=Glycans
(functions: store, structure and recognition)
polymers of monosacc & deriv's
starch,glycogen: storage
chitin, cellulose: structure
surface polysacc: recognition
Starch
(amylose has alpha (1,4), one reducing end and alpha (1,6)
2 forms:amylose & amylopectin
10-30% amylose (linear)
70-90% amylopectin
Glycogen
constitutes 10% liver mass and 1-2% muscle mass
diff from starch: # branches
alpha(1,6) branches every 8-12 residues
like amylopectin is red-violet with iodine
Structural Polysaccharides
(similar to storage polysacc)
cellulose:most abundant natural polymer on earth, principle strength of trees
(has beta complex, linear)
Chitin
exoskeletons of crustaceans, insects and spiders, cell walls of fungi.
similar to cellulose but C2's are N-acetyl
can be parallel or anti
glycosaminoglycans
repeating disacc with amino sugars and (-) charges
glycoproteins
O-link sacc:mannose, galact, xylose
N-link: mannose triad