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Carbohydrates Aka Saccharides Number

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  twitter: @nursehoomantelegram: @zxggeh CARBOHYDRATES o a.k.a. SACCHARIDES o (CH2O)n  n – number of atoms in a unit  CH2O – hydrated carbon o Major energy cycle of life FUNCTION :1.energy storage/generation2.structural3.molecular recognition CLASSIFICATION :1. MONOSACCHARIDE  – one polymer 2. OLIGOSACCHARIDE  – few polymer 3. POLYSACCHARIDE  – many polymer  MONOSACCHARIDE – named by bases on the number of carbon atoms*simplest form: TRIOSE *more biologically important: HEXOSE & PENTOSECLASSIFICATION OF MONOSACCHARIDESA. ACCORDING TO THE GROUP ATTACHING TO IT:1.ALDOSE   Aldehyde group (CHO)  (-ose) 2.KETOSE  Keto group (C=O)  (-ulose) except FRUCTOSE B. ACCORDING TO THE NUMBERING 1. ALDOSE  – C1 is attached to the aldehyde group2. KETOSE  – C1 closest to the keto group*ALDOSES are more biologically important STRUCTURES OF MONOSACCHARIDES: o ISOMERS – same formula but different structure o EPIMERS – isomers with structures varying in one position of carbon o C4 – GLUCOSE & GALACTOSE o C2 – GLUCOSE & MANNOSE o ENANTIOMERS – isomers that are mirror images of each other   -- have chiral carbos that can produce D light*natural occurring carbohydrate in D configuration o DIASTEREOISOMERS – possesses more than 1 chiral carbon  - - not mirror imagesEx. D/L erythrose; D/L threose o ANOMERS – isomers that differ in position  - - 5 or 6 carbons (ring structures) -- internal hemiacetal formation*INTERNAL HEMIACETAL FORMATION – process of ring formation 2 WAYS OF FORMING A RING: o Reaction of C1 & C5 via HYDROXYLATION (PYRANOSE RING *5C & 1 O2) o Reaction of C1 & C4 (FURANOSE RING) 5 membered ring CYCLIZATION o Produces asymmetric centric carbon – ANOMERIC o OH & H change (interchange) o C1 – farthest to the right (in ring) o Can produce 2 or more anomeric configuration (alpha and beta) MUTAROTATION o  Alpha can be Beta and vice versa o Change of configuration o  ALPHA – OH is below H o BETA – OH is above H WAYS TO WRITE CARBOHYDRATES: o FISHER PROJECTION – linear  o HAWORTH PROJECTION – ring IMPORTANT MONOSACCHARIDES: o GLUCOSE  (C6H12O6)  Most common HEXOSE  Found in STARCH, CELLULOSE & GLYCOGEN  Found in VEGETABLES, FRUITS, CORN SYRUP & HONEY  Found in DISACCHARIDES, SUCROSE, LACTOSE & MALTOSE o D-GALACTOSE ( C6H12O6)  C4 EPIMER  Obtained from Lactose; disaccharide   An aldohexose not found free in nature   Attach to glucose as lactose o FRUCTOSE ( C6H12O6)  Ketohexose/ketose  Sweetest carbohydrate  Found in fruits and honey  Converted to glucose in the body DERIVATIONS OF MONOSACCHARIDES:* modified; plays important role o PHOSPHATE ESTERS  PHOSPHORYLATION OF MONOSACCHARIDES   ATP, AMP, nucleic acid o ACIDS & LACTONES  OXIDATION OF MONOSACCHARIDES  Produces GLUCORONIC ACID o ALDITOLS  REDUCTION OF MONOSACCHARIDES  Produces SORBITOLS o AMINO SUGARS  Sugar with amino group  Monosaccharide with amino groups  Ex. GLUCOSAMINE – better cartilage OLIGOSACCHARIDE – linked monosaccharides GLYCOSIDIC BOND o Links monosaccharides o Formed by removing water *DISACCHARIDE GROUP – important group LACTOSE – formed by GLUCOSE & GALACTOSE  twitter: @nursehoomantelegram: @zxggeh NAMING OLIGOSACCHARIDES: o Non-reducing sugars first o From left-right o PREFIX: ALPHA   or BETA o SUFFIX: pyranose, furanose o  –cyl o LINKAGE: (1,4) *pyranocyl, furanocyl 1 mono + 1mono = disaccharides Ex. Glucose + glucose = Maltose Glucose + galactose = Lactose COMMON DISACCHARIDES: GLUCOSE + FRUCTOSE = SUCROSE(1,4) GLUCOSE + GLUCOSE = MALTOSEGLUCOSE + GALACTOSE = LACTOSE(1,4) GLUCOSE + GLUCOSE = CELLOBIOSE(1,6) GLUCOSE + (1,4) GLUCOSE = ISOMALTOSE POLYSACCHARIDE o Structural o Catalyzed by enzymes o Polymers of saccharide linked by glycosidic bond o Storage form of sugar ex. Glycogen & starch STORAGE: o AMYLOSE  Polysaccharide; storage form of sugar in plant (starch)  Saccharide link by ALPHA-1,4-GLYCOSILIC BOND  Polysaccharide arrange in linear manner linked by  ALPHA-1,4-GLYCOSIDIC BOND  Found in potato & starch o AMYLOPECTIN  Polysaccharide arranged in branch manner or structure linked by ALPHA-1,4-GLYCOSIDIC BOND  Branch structure ALPHA-1,6-GLYCOSIDIC BOND  Found in starch o GLYCOGEN  Polysaccharide found in LIVER & MUSCLE  Storage form of glucose in body  Branched: formed by Glycosidic Bond: ALPHA-1,4 &  ALPHA-1,6  Not found in potato GLUCOSE o High osmotic pressure o Small molecule, GLUCOGEN – semi-soluble (do not change osmotic pressure, ready to use when metabolism is acquired) GLUCOGEN -> GLUCOSE STRUCTURAL: o CELLULOSE  Polysaccharide found in plants  Linked by BETA-1,4 glycosidic bond  α-glycosidase – can only break α bonds; found in man  β -glycosidase – can only break β bonds; found in cows, goats, etc.  cow’s intestinal tract has bacteria that produce BETA glycosidase o CHITIN – polysaccharide found in shell, invertebrate, insect and fungi o PEPTIDOGLYCAN – polysaccharide in the cell wall of bacteria o GLYCOSAMINOGLYCAN – they form the matrix of connective tissue MOLECULAR IDENTIFICATION:GLYCOPROTEIN – protein linked to sugar/carbohydrate 2 FORMS: o O– LINKED – sugar is attached to protein through SERINE/ THREONINE o N-   LINKED – sugar is attached to protein through  ASPARGINE*ER – produce proteins* GOLGI COMPLEX – modifies proteins FUNCTION OF N-LINKED o Identify cell surface (IMMUNOGLOBULIN) o TIME CLOCK – signals for digestion (phagocytic cells) o INTRACELLULAR TRANSPORT SIGNAL (labeling proteins) FUNCTION OF O-LINKED o  Anti-freeze substance o Increases viscosity of secretion *MUCIN* o INTRACELLULAR TRANSPORT SIGNAL
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