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Glycobiology_Course_lesson_1

Glycobiology_Course_lesson_1 - Glycobiology Course 1...

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Unformatted text preview: Glycobiology Course 1 Introduction Roland Contreras Nico Callewaert Wouter Laroy Introduction Introduction Paper, cotton, photgraphic films, … It’s sugar! Introduction Food products It’s sugar! Introduction Genetic code It’s sugar! Introduction Energy - glycogen It’s sugar! Introduction The erythrocyte glycocalyx It’s sugar! Introduction ABO Blood groups It’s sugar! Introduction Influenza It’s sugar! Introduction Xenotransplantation It’s sugar! Introduction Chagas disease It’s sugar! Introduction Evolution It’s sugar?! Introduction Fertilization It’s sugar! Introduction Inflammation • Rolling of neutrophils • Rolling of neutrophils 2 It’s sugar! Carbohydrates Carbohydrates (CH 2 O) n Monosaccharides: simple sugars with multiple OH groups. Based on number of carbons (3, 4, 5, 6), a monosaccharide is a triose, tetrose, pentose or hexose . Disaccharides: 2 monosaccharides covalently linked. Oligosaccharides: a few monosaccharides covalently linked. Polysaccharides: polymers consisting of chains of monosaccharide or disaccharide units. Carbohydrates: aldose/ketose Aldose: Aldehyde at one end Ketose: Keto group usually at C2 D-Glucose D-Fructose 1 2 3 4 5 6 1 2 3 4 5 6 Fischer projection Carbohydrates: Epimers OH HO OH OH CH 2 OH O HO HO OH OH CH 2 OH O HO HO HO OH CH 2 OH O D-Glucose D-mannose D-Talose diastereomers epimers epimers Epimers: isomers that differ in only one carbon configuration Carbohydrates: Stereoisomers Aldotriose D-glyceraldehyde L-glyceraldehyde D-glucose L-glucose Aldohexose D & L designations are based on the configuration about the single asymmetric C in glyceraldehyde For sugars with more than one chiral center, D or L refers to the asymmetric carbon farthest from the aldehyde or keto group D and L sugars are mirror images of one another and are called enantiomers Most naturally occurring sugars are D enantiomers Carbohydrates: Stereoisomers D and L sugars are mirror images of one another and have the same name • D-Glucose and L-Glucose Stereoisomers on other positions have different names • Glucose, galactose, fucose, … The number of stereoisomers of a carbohydrate is 2 n (n=number of asymmetric centers) • C 6 aldoses (hexose) have 4 asymmetric centers and 16 stereoisomers (8 D + 8 L) Carbohydrates: Stereoisomers Carbohydrates: Diastereomers Diastereomers: Isomers that have opposite configuration at one or more carbons but are not mirror images OH HO OH OH CH 2 OH O HO HO OH OH CH 2 OH O HO HO HO OH CH 2 OH O D-Glucose D-mannose D-Talose diastereomers epimers epimers Carbohydrates: Ring formation Aldehyde + Alcohol ↓ Hemiacetal Ketone + Alcohol ↓ Hemiketal Carbohydrates: Ring formation Pentoses and hexoses can cyclize • Ketone or aldehyde react with distal hydroxy group 6-member ring: Pyranose 5-member ring: Furanose Cyclic form: Haworth projection Carbohydrates: Ring formation Haworth projection Carbohydrates:...
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Glycobiology_Course_lesson_1 - Glycobiology Course 1...

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