Chapter 7 - Chapter 7 Monosaccharides o hexose sugars are...

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Chapter 7 Monosaccharides o hexose sugars are the most abundant in nature o the simplest monosaccharides are water soluble and most taste sweet o enantiomers – D and L configurations are mirror images of each other o epimers – 2 sugars that differ in configuration at only one chiral center o diastereomers – pair of isomers that have opposite configurations at 1+ chiral centers but that aren’t mirror images of each other o cyclic hemiacetals of aldohexose sugars generally form pyranoses and cyclic hemiketals of ketohexose sugars generally form furanoses cyclic structures w/ less than 5 sides or more than 6 sides are generally too strained to form the chair or boat structures of the pyranose depends on putting bulky substituent groups at equatorial positions rather than axial positions (but chair is more stable than boat) o anomers – isomers that differ only in their configuration about the anomeric carbon atom (when the sugars in their cyclic forms) α – -OH at anomeric carbon is on the same side of a Fischer projection as the O atom at the highest numbered asymmetric carbon
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