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Biochemistry Ch. 4 - Carbohydrate Structure and Function
MCAT
30
Biochemistry
Undergraduate 3
06/07/2016

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Term
aldoses
Definition
carbohydrates that contain an aldehyde as their most oxidized group
Term
ketoses
Definition
carbohydrates with a ketone as their most oxidized group
Term
D-fructose
Definition
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Term
D-glucose
Definition
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Term
D-galactose
Definition
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Term
D-mannose
Definition
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Term
D and L naming convention with sugars
Definition
sugars with the highest-numbered chiral carbon with the -OH group on the right (in a Fischer projection) are D-sugars; those with teh -OH on the left are L-sugars; D and L forms are enantiomers
Term
diastereomers
Definition
differ at at least one-but not all-chiral carbons; these include epimers and anomers
Term
epimer
Definition
a subtype of diastereomer that differs at exactly one chiral carbon
Term
anomer
Definition
a subtype of epimer that differs at the anomeric carbon
Term
How is the (+) or (-) convention determined?
Definition
It must be experimentally determined and can't be determined from D or L designations
Term
pyranose
Definition
six-membered ring
Term
furanose
Definition
five-membered rings
Term
Do sugars exist in predominantly cyclic or linear form?
Definition
cyclic
Term
How to determine the anomeric carbon
Definition
the new chiral center formed in the ring closure; it was the carbon containing the carbonyl in the straight-chain form
Term
How to determine α vs. β anomers
Definition
  • alpha have the -OH on the anomeric carbon trans to the free -CH2OH
  • beta have the -OH on the anomeric carbon cis to the free -CH2OH
Term
mutarotation
Definition
occurs when hemiacetal rings are exposed to water; they spontaneously cycle between the open and closed forms allowing either the alpha or beta anomer to form; occurs more rapidly when catalyzed with acid or base
Term
reducing sugars
Definition
any monosaccharide with a hemiacetal ring; this is becuase aldoses can be oxidized making them a reducing agent
Term
What does Tollen's reagent test for?
Definition
  • aldehyde groups
  • alpha hydroxy ketone functional groups
Term
What does Benedict's reagent test positive for?
Definition
  • alpha hydroxy ketone groups
  • aldehyde groups
Term
enol
Definition
compound with a double bond and an alcohol group
Term
esterification of sugars
Definition
the hydroxyl groups of sugars can form esters by reacting with carboxylic acids and carboxylic acid derivatives
Term
tautomerization
Definition
the rearrangment of bonds in a compound
Term
glycoside formation in sugars
Definition
the basis for building complex sugars and requires the anomeric carbon to link to another sugar; occurs when hemiacetals or hemiketals react with alcohols to produce acetals and ketals
Term
sucrose
Definition

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glucose-α-1,2-fructose

Term
lactose
Definition

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galactose-β-1,4-glucose

Term
maltose
Definition

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glucose-α-1,4-glucose

Term
cellulose
Definition
  • polysaccharide composed of β-D-glucose molecules linked by β-1,4 glycosidic bonds

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Term
amylose and amylopectin
Definition
  • amylose is a lineaer α-D-glucose polymer linke via α-1,4 glycosidic bonds
  • amylopectin is the same but contains branches connected by α-1,6 glycosidic bonds 

[image]

Term
glycogen
Definition
  • similar to starch in that it uses α-D-glucose molecules connected by α-1,4 glycosidic bonds
  • contains more α-1,6 glycosidic bonds making it more highly branched
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