Glycobiology_Course_lesson_1

Glycobiology_Course_lesson_1 - Glycobiology Course 1...

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Glycobiology Course 1 Introduction Nico Callewaert
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Introduction
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Introduction 9 Paper, cotton, photographic films, … It’s sugar!
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Introduction 9 Food products It’s sugar!
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Introduction 9 Genetic code It’s sugar!
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Introduction 9 Energy - glycogen It’s sugar!
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Introduction The erythrocyte glycocalyx It’s sugar!
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Introduction 9 ABO Blood groups It’s sugar!
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Introduction 9 Influenza It’s sugar!
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Introduction 9 Xenotransplantation It’s sugar!
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Introduction 9 Chagas disease It’s sugar!
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Introduction 9 Evolution It’s sugar?!
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Introduction 9 Fertilization It’s sugar!
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Introduction 9 Inflammation Rolling of neutrophils Rolling of neutrophils 2 It’s sugar!
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Carbohydrates 9 (CH 2 O) n 9 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 . 9 Disaccharides: 2 monosaccharides covalently linked. 9 Oligosaccharides: a few monosaccharides covalently linked. 9 Polysaccharides: polymers consisting of chains of monosaccharide or disaccharide units.
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Carbohydrates: aldose/ketose Aldose: Aldehyde at one end Ketose: Keto group usually at C2 1 2 3 4 5 6 1 2 3 4 5 6 D-Glucose D-Fructose Fischer projection
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Carbohydrates: Epimers Epimers: isomers that differ in only one carbon configuration 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
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Carbohydrates: Stereoisomers D-glyceraldehyde L-glyceraldehyde D & L designations are based on the configuration about the single asymmetric C in glyceraldehyde Aldotriose For sugars with more than one chiral center, D or L refers to the asymmetric carbon farthest from the aldehyde or keto group D-glucose L-glucose O H O H C C H – C – OH HO – C – H HO – C – H H – C – OH H – C – OH HO – C – H H – C – OH HO – C – H CH 2 OH CH 2 OH D and L sugars are mirror images of one another and are called enantiomers Aldohexose Most naturally occurring sugars are D enantiomers
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Carbohydrates: Stereoisomers 9 D and L sugars are mirror images of one another and have the same name • D-Glucose and L-Glucose 9 Stereoisomers on other positions have different names • Glucose, galactose, fucose, … 9 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)
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Carbohydrates: Stereoisomers
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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
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Carbohydrates: Ring formation O C H R O H O C R R' O H C R R' O aldehyde alcohol hemiacetal C H R O R' R' O H "R O H "R + + Aldehyde + Alcohol Hemiacetal Ketone + Alcohol Hemiketal
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Carbohydrates: Ring formation 9 Pentoses and hexoses can cyclize • Ketone or aldehyde react with distal hydroxy group 9 6-member ring: Pyranose 5-member ring: Furanose 9 Cyclic form: Haworth projection
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Carbohydrates: Ring formation Haworth projection
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Glycobiology_Course_lesson_1 - Glycobiology Course 1...

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