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carbohydrates that contain an aldehyde as their most oxidized group |
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carbohydrates with a ketone as their most oxidized group |
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D and L naming convention with sugars |
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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 |
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differ at at least one-but not all-chiral carbons; these include epimers and anomers |
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a subtype of diastereomer that differs at exactly one chiral carbon |
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a subtype of epimer that differs at the anomeric carbon |
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How is the (+) or (-) convention determined? |
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It must be experimentally determined and can't be determined from D or L designations |
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Do sugars exist in predominantly cyclic or linear form? |
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How to determine the anomeric carbon |
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the new chiral center formed in the ring closure; it was the carbon containing the carbonyl in the straight-chain form |
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How to determine α vs. β anomers |
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- 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
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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 |
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any monosaccharide with a hemiacetal ring; this is becuase aldoses can be oxidized making them a reducing agent |
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What does Tollen's reagent test for? |
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- aldehyde groups
- alpha hydroxy ketone functional groups
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What does Benedict's reagent test positive for? |
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- alpha hydroxy ketone groups
- aldehyde groups
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compound with a double bond and an alcohol group |
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the hydroxyl groups of sugars can form esters by reacting with carboxylic acids and carboxylic acid derivatives |
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the rearrangment of bonds in a compound |
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glycoside formation in sugars |
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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 |
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[image]
glucose-α-1,2-fructose |
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[image]
galactose-β-1,4-glucose |
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[image]
glucose-α-1,4-glucose |
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- polysaccharide composed of β-D-glucose molecules linked by β-1,4 glycosidic bonds
[image] |
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- 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] |
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- 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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