Aula 17 Carboidratos

1 mol of maltose\nA disaccharide\n\n2 mol of glucose\nA monosaccharide\n\n1 mol of sucrose\nA disaccharide\n\n1 mol of glucose + 1 mol of fructose\nMonosaccharides\n\n1 mol of starch or 1 mol of cellulose\nPolysaccharides\n\nmany mols of glucose\nMonosaccharides x CO2 + y H2O + solar energy → Cx(H2O)y + x O2\nCarbohydrate\n\nCx(H2O)y + x O2 → x CO2 + y H2O + energy Adenine\n\nADP\n\nRibose\n\nDiphosphate\n\nChemical energy from oxidation reductions\n\nHydrogen phosphate ion\n\nATP\n\nNew phosphoric anhydride bond\n\nH2O\n\nR—C—OH + ATP → R—C—O—P + ADP\n\nAn acyl phosphate An aldose\n\nA ketose\n\nAn aldopentose\n\nAn ketopentose\n\nGlyceraldehyde (an aldotriose)\n\nDihydroxyacetone (a ketotriose) (+)-Glyceraldehyde\n\n(−)-Glyceraldehyde\n\nA D-aldopentose\n\nAn L-ketohexose\n\nHighest numbered stereogenic center H H H H H\nH | | | | O\nH | | | | H\nH - C - OH\n | | \n OH H\n | |\n C - C\n | |\n H O\n | \n H\n | \n C - C - O\n | | \n H H H\n | \n OH\n | \n H\n | \n H\n | \n O \n | \n H\n | \n H\n | \n O\n |\n OH\n \nFischer projection formula\nCircle-and-line formula\nWedge-line-dashed wedge formula\n1 2 3 4\nStructural representations\n5\nα- and β-D-glucopyranose\n6 7 \n H H\n| |\nOH | \n| H\n| | OH\n| C\n| |\nOH C\n | O H\n | | \n OH HO \n | H\n OH\n | \n H \nH A pyran \nFuran Glucose\n\n[plane projection formula]\nWhen a model of this is made it will look as follows:\n\nIf the group attached to C4 is pivoted as the arrows indicate, we have the structure below.\n\nThis —OH group adds across the =C=O bond to form a new Si atom and make a cyclic hemiacetal.\n\nOpen-chain form of α-D-glucose\n\n(pyranose = is the hemiacetal form)\n\nβ-D-4-deoxyglucose\n(same —OH is the hemiacetal —OH, which is β-D-glucose on the same side of the ring as the —CH2OH group at C5.) α-D-(+)-Glucopyranose\n(mp 146°C; [α]D25 = +112°)\n\nOpen-chain form of D-(+)-glucose\n\nβ-D-(+)-Glucopyranose\n(mp 150°C; [α]D25 = +18.7°) α-D-(+)-Glucopyranose\n(36% at equilibrium)\n\nβ-D-(+)-Glucopyranose\n(64% at equilibrium)\n\nα-D-Mannopyranose\n(69% at equilibrium)\n\nβ-D-Mannopyranose\n(31% at equilibrium) D-Glucose\n(open-chain form)\n\nD-Manose\n\nEnolate ion\n\nD-Fructose\n\nEnediol Reducing Sugar\nHemiacetal (R' = H or = CH2OH)\n(gives positive Tollens' or Benedict's test)\n\nNonreducing Sugar\nAcetal (R' = H or = CH2OH)\n(does not give a positive Tollens' or Benedict's test)\n\nAlkyl group or another sugar CHO\n(CHOH)n\nCH2OH\nAldose\n\nCH2OH\n(CHOH)n\n(CHOH)m\nAlditol\n\nD-Glucitol (or D-sorbitol) H\n\n C=NNH2\n | \n C1HNH2 + C6H13NH2 + H2O\n\n Aldose Phenylosazone\n\n (formed from the aldose)\n\n\n H\n C=NNH2\n |\n C1-N-C3H5\n | \n C2H5\n tau t\n C=O\n H\n CH-NH\n C=O\n (+2C2H5NH2) \n\n CHO\n |\nH-OH\n | CH=NNH2\nH-OH |\nH-OH-C1=NNH2\nH-OH |\nH-OH\n CH2OH\n | \n CH2OH\n D-Glucose\n \nSame phenylosazone\n D-Mannose\nCHO\n |\nH-OH\n | \nH-OH\n H-OH\n |\n H-OH\n CH2OH From D-glucose\n\n α-Glucosidic linkage\n \n \nFrom D-fructose\n β-Fructosidic linkage\nH\nO\nH\nOH OH\nCOH O\nH H\n C1H2OH C2H5OH\nH OH\nH\nH\n O\n OH\n H α-Glucosidic linkage or\n\nβ-Glycosidic linkage α(1 → 4) Glucosidic linkage\n\nn > 500 Branch\n\nMain chain\n\nα(1 → 6) branch point\n\nα(1 → 4) β(1→4)\n 6CH2OH \n 5\n O\n 5\n H\n H\n H\n H\n O\n H\n OH\n 6CH2OH\n 5\n 6\n 6\n 6\n 6\n n Fuente: Unica/ unidades proditoras\n\n5,300\n4,200\n1980\n1986/1988\n2003 R' + H2N−R' → Aldehyde or ketone + 1° Amine → [R'−C−NHR] OH → Hemiaminal → [R'−C=NR'] + H2O → Imine → [H] → R'−CH−NHR → 2° Amine H-C=O + RNH2 → H-C(OH)−NHR \n→ H-C(OH)−NHR \nAmadori compound \n→ H2O \n→ Amadori compound\n3-deoxyosone \nFurfural \n5-Hydroxymethylfurfural Tyrosine → (C4 enzyme) → DOPA → (O2 enzyme) → DOPA Quinone \n→ (fast) \n→ Leuco compound \n→ (slow) \n→ Melanin \n→ 5,6-diacyldopyl \n→ Indole 5,6-quinoids \n\n{Images: Pretzels, Potatoes, Cream}