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D to L
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Need to flip all chiral centers (enantiomers)
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Enantiomers
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Stereoisomers that differ in arrangement of groups around all chiral centers
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Anomers
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Stereoisomers that differ only in arrangement of groups around the anomeric Carbon
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Anomeric Carbon
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Carbon that was either part of an aldo or keto group in a linear sugar that has cyclized
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Hemiacetal (or hemiketal)
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Cyclized sugars (hemiacetal = aldehyde and alcohol) (hemiketal = keto group and alcohol)
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Alpha designation vs. beta designation
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Alpha = OH group on the anomeric carbon is in the same configuration as the ring oxygen. Beta = OH and the ring O are in the opposite configuration
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Drawing Fischer Projections
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1) Put the anomeric C at the top of the chain
2) OH that's down on Haworth is put on the right side of the molecule
3) OH that's up on Haworth is put on the left side
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Pyranose
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6 membered ring carbohydrates
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Furanose
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5 membered ring carbohydrates
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Mutarotation
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Conversion between different anomeric forms in solution
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Reducing sugars
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Sugar and sugar derivatives that have free anomeric OH groups.. called this because they can reduce metal ions such as Cu+2 or Fe+3
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Original assay for serum or urinary glucose
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Based on its ability to reduce Cu+2 to Cu(I)2O (a red precipitate) --> not very specific
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-oside ending on a sugar
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Indicates no longer a free anomeric OH group
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Modern assay for glucose
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Reaction contains: urine or blood sample, glucose oxidase (very specific for beta-D-glucopyranose), a dye capable of reducing peroxide and changes color, peroxidase (enzyme that catalyzes peroxide reduction), and mutarotase (enzyme that catalyzes mutarotation)
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O-glycosides
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Formed by the reaction of the anomeric OH group of sugar units with the alcohol groups of other molecules (often part of other monosaccharides that cannot mutarotate) *reaction not spontaneous under STD state conditions but can proceed in vivo
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