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35 Cards in this Set
- Front
- Back
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monosaccharide
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single carbohydrate unit
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dissacharide
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2 carbohydrate units
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oligosaccharides
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short carbohydrate chains
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polysaccharides
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long carbohydrate chains
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carbohydrates end in suffix -ose
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know
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aldose = aldehyde sugar
the aldehyde will always start with number 1 when naming.. |
know
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monosaccharides are characterized by the number of carbons they have
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know
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ketose = ketone sugar
ketonw will receive the lowest number when numbering = 2 |
know
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D-sugars demonstrate a positive/negative rotation
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positive
D(+) |
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L-sugars demonstrate a positive/negative rotation
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negative
L(-) |
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all other chiral carbons are either D or L, depending on if they are in the same configuration as the 1st carbon
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ex)
if the 1st carbon has a D(+) rotation and the 3rd carbon has the same configuration as the D(+) 1st one, then the 3rd one is also D(+) |
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all D sugars will have the hydroxides of their highest numbered chiral center on the left/right
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right
highest number meaning furthest from top |
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all L sugars will have the hydroxides of their highest numbered chiral center on the left/right
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left
"L" = LEFT highest meaning furthest from top ....refer to pg 257 top |
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rules about sugars
1. the same sugar structures that are in different optical families (L and D) are enantiomers 2. all non-identical(non-mirror image) sugars within the same family that are of the same type(ketoses or aldoses) and have the same number of carbons are diastereomers 3. diastereomers that only differ by one chiral center arrangement(S -->R etc) = epimers (make up same family; both D or both L) |
1. ex) L-glucose is an enantiomer of D-glucose
2. :( 3. agh |
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draw:
1. D-fructose 2. D-glucose 3. D-galactose 4. D-mannose |
refer to pg 258
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ring properties
because monosaccharides contain both a hydroxyl(nucleophile) and a carbonyl(electrophile) they can form cyclic rings |
hemiacetal = aldoses --> rings
hemiketals = ketoses --> rings |
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due to ring strain, there are only 2 structures that are "stable"...
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1 = 6-membered pyranose rings
2 = 5-membered furanose rings |
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pyranose ring forms ____ configuration and the substituents are in either the axial or equitorial positions
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chairlike
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look and read pg 258 explaining fischer --> haworth projection drawing
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pg 258
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6-membered rings formed from _Carbon aldoses and _Carbon ketoses
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6
7 |
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5-membered rings are formed from _C aldoses and _C ketoses
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5
6 |
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anomers are cyclic stereoisomers that differ about the new chiral carbon formed
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http://www.cartage.org.lb/en/themes/Sciences/Chemistry/Organicchemistry/Common/anomer.gif
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the anomeric carbon is the one new chiral carbon formed in the cyclic formation
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know
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the anomeric carbon can be easily found within a structure or drawing..its the carbon attached to both the Oxygen in the ring and a hydroxyl group
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http://www.cartage.org.lb/en/themes/Sciences/Chemistry/Organicchemistry/Common/anomer.gif
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the alpha-anomer has the hydroxyl attached to the anomeric carbon in trans arrangement with the CH2OH
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http://www.nku.edu/~russellk/tutorial/sugar/alla.gif
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the beta-anomer has the hydroxyl group attached to the anomeric carbon in cis with the CH2OH
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http://www.nku.edu/~russellk/tutorial/sugar/glub.gif
both point up/down |
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hemiacetal rings + h2o =
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spontaneous opening of ring and reformation occurs
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the carbon-carbon bond between ring and CH2OH can/can not rotate freely to allow alpha or beta formation
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can
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reformation that results in a different arrangement (alpha --> beta etc) =
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mutarotation
-occurs rapidly when catalyzed with acid/base |
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mutarotation results in a mixture that contains both anomers at their EQ concentrations
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know
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the alpha/beta arrangement is less favored because the OH- group of the anomeric carbon is axial; adds to steric strain
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alpha
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treat monosaccharides with OH groups like carbon-chained alcohols...will react just the same
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know
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for rxn details, refer to pg 260-264
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LOL
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woot
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woof
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doof
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poof
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