= ‘a Poy rmesose Ft pas the molecular formula CylH,.05. On a tte ‘pemical propertics it was found : q Pentain aketonic functional group CH2OH fe : : <0 1 yeastraight chain of six carbon Holy Hon pe ne case of glucose. i . jbl Song to D-series and a y_4_ {1 compound: Therefore, it is L = sity written as D-(-)-fructose. ts ppt, (tt soture is shown on R. H. S, port structure for Fructose. Like gl ne struc slucose, forms internal ketal by the intramolecular 2 stketo group and ~ OH group of Gg atom, As ey exomes chiral. Thus, fructose has two possible D- (-) fructose and f-D--) fructose which gs a 4 i arrangement of ~ CH,OH and -OH groups fies. ‘These two isomers are shown in Fig. 17.3. B-D-Fructose 4 4 a 6 4 4 e G _ a oO 1 CHZOH rz Gy ie on OHH a-D-Fructose fee neep Fig. 17.3 Structure of « and B-D(-) fructose. Inthe free state, D-fructose exists as a six membered Zot as pyranose ring as shown in Fig.17.3. However, in ‘onbined state as a constituent of disaccharides, it exists befuranose form (5-membered hemiketal) as shown in -N14 and 17.5, Tt ean be obtained by internal ketal re by combining keto group (of C-2) and-OH group s| 6| HOH ‘CH2OH sg. iotranose [casera 24Fschor projection formulae of a andP-fructoturanose: -0-Fructose Fig.17.5 Howarth projection. formutae deka ats ‘end tructoturanose ‘These cyclic structures ean also be writ tae written in the same Uses of (-) Fructose. Fructose is used (i) as a substitute for cane sugar by diabetic patients, (ii) as a sweetening agent in confectionary. DISACCHARIDES ey Disaccharides are the compounds which on hydrolysis, with dilute acids or enzymes yield two molecules of either same or different monosaccharides, e.g., CigH20}1 + HO Coty + CoH 20 Matos Glucose” QLACO DL, CygH 30), + H90 > CgHy206 + CoH 1206 Suctone Gucwe” Frise CigHy:041 +20 > Celta + CoH i206 Lactose Giucose” — Galaciose ‘These are formed by the condensation reaction between two molecules of the same or different monosaccharides and involve the formation of an acetal from a hemiacetal and an alcohol with the elimination of the water. In this reaction, one molecule of the monosaccharide acts as the hemiacetal while the other acts as the alcohol. The new linkage formed is called the glycosidic linkage. X/“” The disaccharides may be reducing or non-reducing depending upon the position of glucosidic linkage between two monosaccharide units. Ifthe glycosidic linkage is formed between the carbonyl functions of both the monosaccharide units, the resulting disaccharide would be non-reducing, €.8. sucrose. If one of the carbonyl functions in any one of the monosaccharide units is free, the resulting disaccharide would be reducing in nature, e.g., maltose and lactose. Sucrose (Cane Sugar), CyzH22011 ‘Sucrose (ordinary table sugar) is the most common icaccharide widely distributed in plants. It occurs in sugar one (16-20%), agar beets (10-15%), pine apples (10-12%), apricot, banana, mango and honey. It is tnanufactured from sugar cane (which grows in tropical Countries like India and Java) or beet root (which grows in cold climates). Sucrose is a colourless, odourless, crystalline sweet substance having mp, 185-186°C. It is soluble in water but practically insoluble in alcohol and ether. Inversion of sugar. Sucrose is dextrorotatory with a specific rotation, [aly = + 66.5°. On hydrolysis in presence of HCl or enzyme invertase or sucrasem, it givesan equimolar mixture of glucose with a specific rola/i0® aly = + 52.7 and fructose with a specific rotation, [@'p = ~ 924°, Since the specific rotation of D(+) glucosé 18 Tess than that of D-C) fructose, the resulting solution afte? hydrolysis becomes laevorotatory. Since the hydrolysis ©, suerose to an equimolar mixture of D-(+) glucose ant, (D)-() fructose is accompanied by the change in sien © optical rotation from dextrorotatory to laevorotatoryy hydrolysis of sucrose is called inversion of sugar an the equimolar mixture of D-(+) glucose and D-(-) fructose obtained as a result of hydrolysis is called invert sugar. CygHax0)) + HO AS CoH 1206 + ColHl126 [al = +665 rye Dyt)-Civeose _ D-CIFroetose [alp = +527 [aly =-924 Fermentation. Aqueous solution of sucrose on fermentation with yeast, gives ethyl alcohol and carbon dioxide. The enzyme invertase (present in yeast) first converts sucrose into glucose and fructose. Another enzyme zymase (also present in yeast) then converts glucose and fructose into ethyl alcohol with the evolution of carbon dioxide. CygHa2011 + H20 FP Cott 206 + CoHi206 Bere Ghusoe Fructose C6Hj20, 2+ 2C) HOH +2C0) It may also be noted that sucrose does not act as reducing agent and does not form anycyanohydrin or oxime Structure. Sucrose on hydrolysis yields a mixture of equal parts of glucose and fructose. This shows that sucrose molecule is made by the combination of one glucose and one fructose molecule with the elimination of a water molecule as shown in Fig. 17.6. These two monsaccharides gfe held together by glycosidic linkage between C; of on Ghessae ieee cHeOH @-D-Frictotzaroce) ‘a Hodg b ° Ho nfo woe pow TE Hcy i 4 ch SC CHEMISTRY pp cy of fefructose. Since, the reduc cogs nd oe oee are involved in glyeosige = of gluston, sucrose is a non-reducing SUN ns (Ornerges of Sucrose. Sucrose is used = toaa food and as a sweetening agent, (Ot a preservative for food prods such as Jay, dips the laboratory preparation of oxalic aig, ™ (Gay for denaturing alcohol and to render pop, transparent and oil repellant. : Meats.) Charring test. Take a pinch ofthe organ compound and add to it 1 mL of cone. HaS0,, Chains place. Tarvin takes oD Led acetate test. To mL of aqueous solution of the compound, add 1 mL of lead acetate solution and exes, of NH,OH-A white ppt. in Nickel sulphate test. Boil 0.1 gof the compoung with canmoniaeal nickel sulphate solution Add di H,so, Solution - a red colour. " tiv) Cobalt nitrate test. Warm 1 mL of the aqueous solution of the compound with 1 mL of NaOH solution and Solew drops of cobalt nitrate solution -a violet colouration. ole ose (Malt Sugar), CyzH22011 Itis obtained by the partial hydrolysis of starch by diastase, an enzyme present in malt which is obtained from sprouted barley seeds. 2(CH 90s). + HO PB nC 2H320), ‘stch ; Matoxe Maltose on hydrolysis yields two molecules of a-D-(+) glucose. This indicates that maltose (malt sugar) is formed by the condensation of two molecules ofa-glucose in which C, of one a-glucose unit is connected to C, of the other through an a-glycosidic linkage. RT Fig. 17.7 Formation and structure of maltose.gouotecuLes poth glucose units are in pyranose form and maltose pequeing sugar. The form, ind structure of is 8 "is shown in Fig, 17.7, AZ (Milk Sugat), CypH920 sy actase ovcurs in the milk ofall animals and is also % gi milk sugar: Cow's milk contains 4 to 6 pereent and ‘an milk contains 5 to 8 percent lactose. Unlike other wichyadrates, it is not found in plants. Lactose on hydrolysis with dilute acid or emulsin enzyme which specifically hydrolyses p-glycosidie 1H ages) produces one molecule of f-D-galactose and one ule of B-D-glucose. This indicates that lactose is ined by combining a glucose unit and a galactose unit ih the elimination of water as shown in Fig. 17.8. The sniage is between C of galactose and Cy of glucose, Hence, jose is called a reducing sugar. ED 800015 wit rtatve swoctnss, ‘Sugar Relative ‘Sugar Relative ‘Sweetness ‘Sweetness Fructose 173 Galactose 82 Sucrose 100 Maltose 32 Glucose 14 Lactose 16 GA YOLYSACCHARIDES hy ‘hese compounds give a very lar; a /e a very large number of ‘monosaccharide molecules on acidie hydrolysis, Cellulose and starch are two important examples of polysaccharides heir general formula is (CeHjgO,), where n isan intogey having very high value (CoH o0s),, + 0,0 nC gH,.05 Starch or elalove Gucose Polysaccharides are generally amorphous, tasteless substances which are insoluble in water. On complete hydrolysis in presence of acids or enzymes, they change into monosaccharides. ‘Three important examples of the polysaccharides are: starch, cellulose and glycogen. Starch (Amylum), (CgH,g05),. It occurs in plants inthe form of granules which are found mainly in the seeds, fruits, tubers and roots of the plants. It is a mixture of two polysaccharides, i.e, amylose (20%) and amylopectin (80%). Amylose is water soluble while amylopectin is insoluble. Both amylose and amylopectin are polymers of glucose. Amylose is composed of 1003000 D-glucose units linked together to form unbranched chains. On the other hand, Fig. 17.8 Formation and structure of -Lactose. Tsucar AND SWEETNESS Mono as well as disaccharides are sweet in taste. “rent sugars have different degree of sweetness. Fructose the sweetest sugar known (see Table 17.2). Some fuPounds like saccharine which has different chemical ‘ure from carbohydrates is 500 times sweeter than wis? and is used as artificial sweetner. Some proteins Si Peptides are sweeter than sugars. For example, ‘kul protein is 2000 times sweeter than sucrose ‘spartame peptide is 160 times sweeter than sucrose. amylopectin is a branched chain polysaccharide made up of 25-30 D glucose units joined by a-glycosidic linkages H=o: between C-1 of one glucose unit'and C, of the next glucose se Meeay unit as in amylose. However, thé6 chains are connected to lee ° each other by 1, 6-linkages.|The structure of amylose and ° Ho-c—H amylopectin are shown in Fig. 17.9 (a) and (6) respectively. | uA 5 y HA cH ‘i ti (] i moQ OH HW HH om GH0H en Fete SE fae YE #-D-Glactose -D-Glicose Amylose is near polymer of a-D-gucose unts Fig. 17.9(a) Structure of amylose Amylopeetinis a branched chain polymer Fig. 17.9(b) Structure of amylopectin

Tt may be noted that no ‘wo sour starch eder, insoluble Starch is a white amorphous powder, nso in cold water. Its solution in water gives a blue CmeNr with iodine solution. Theblue colour disappearsan Henle and reappears on cooling, On hydrolysis with dite or enzyme, starch breaks down to smaller molocr ee maltose and finally D-glucose. Stareh is @ major food material and is hydrolysed by enzyme amylose pres saliva, The end product is glucose. (CoH 00s) > (Col oOs)at > Cr2H- rend) : Starch does not reduce Fehling solution oF Tolan’ reagent and does not form an osazone. This indicates that all hemiacetal hydroxyl groups of glucose units (C - 1) are linked with glycosidic linkages. It is used as food in the form of bread, cakes, rice and potatoes. It is used in the manufacture of glucose, ethyl alcohol, dextrins and adhesives. Starch is also used in coating and sizing paper to improve its writing qualities. It is also used for stiffening textiles, Starch is used as an indicator for iodometric titrations. The structure of amylose and amylopectin are shown in Fig. 17.9(a) and (b) respectively. Inaddition to starch, many polysaccharides like gum and peetins are used as food components. Gums are polysaccharides which are made up of more than one type of monosaccharides. Gum arabic is available from trees and shrubs. These cause gelling and are used in food industry for the purpose of thickening and improvement to texture. Some gums are used as inert agents (in drug preparation) to suspend an active drug. Difference between gums and other polysaccharides (© Gums are polysaccharides which are made up of more than one type of monosaccharides whereas othor Polysaccharides are made up of only one type of mono. saccharides, Gums are acidic polysaccharides whereas other ‘Charides are neutral. vs give identical 33041 > Calli 206 Ee bine Pol GEWD vitterence between Monosaccharides, 18C CHEMIsy yy " ate nest glucans anit CFE ITO), hy Pony a ep 00 to 6,000,000 correnpond he 5 of 50,000 (0 6,00 rise units joined Cogetlyer® Wood iin glucose U and cellule: GHyOH bon oN % 0 Wy 1 HM 4 on At Wo F Gn LG Pi Hon Mtn Fig. 17.10 Structure of collulose Ti malay N through multiple hydrogen bonds.‘ arith its structure due to which it ean be used tet 1s a cell wall material, ny Cellulose is a colourless amorphous sol Whi decomposes on heating, It does not reduce Tollen', reaga and Fehling’s solution, It does not form osszone nat fermented by yeast Ttis not hydrolysed so easily aan However, on heating with dilute sulphuric acid uxge pressure, it yields D-glucose as the only product Cellulose is used in the preparation of some imprtay products : Us Gun Cotton (explosive). Bir As cellulose acetate-ysed in plastics, raping films, nail polish etc. (iii) As ethyl cellulos¥ tf plastic coats and films, Gv) As methyl cellulose in fabric sizing, cosmeticsand pastes, () Celluloid and rayons. Peetins. These are found in fruit skins and are extracted by boiling them in water. Citrus rends contain 50% pectin. Jelly is prepared by dissolving pectin in rut juice. Here pectin helps jelly to set into a semisolid Pein finds use in drug preparation as inert agent to suspend an fe drug. Glycogen. The polymer consists of hundred to thousand units of glucose. It is the main form in sich slucose is stored in the body. Glycogen mainly oocurs in the oh and liver. It is a short term food reserve in animals fs structure is similar to that of amylopecti iffer fen eCcharides, disaccharides and polysacch differ from each other in many respects. The main points of differences are given in Table 17.3. disaccha ; ee tence Disaccharides es tates eit general formula is|Thelr ; olysaccharides CrHa90, where n is be Grnerel formula is| These are eithe 5(C. ), called are trees ea faa ae C bon wE8 contain 3 to 7 These si hexosans : carbon atoms, moneeanstts eentain twolThese contain m, ides linked iccharide units together by aiecaae monosacchari haa al et ee c linkage in a long cture.