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![H
D-Glucose, cyclic
(D-Glucopyranose)
STEP 1
0-H
D-Glucopyranosyloxy anion
STEP 2 Ring-opening
same as
D-Glucosyloxy anion
STEP 3 |н
i.
[2] Encircle the HEMIACETAL carbon on D-Glucopyranose](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Fab099c87-bf70-4c3d-87ef-08495addc0f9%2F9d9dbc48-b9d1-45b9-b08f-25726fdf62ee%2F8xhwg9_processed.jpeg&w=3840&q=75)
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- ACTIVITY-4. Refer to the structures below. Draw the Haworth formula (pyranose) -OH но H- FOH FOH- но но H- H FOH H FOH- H- CH2OH CH2OH Alpha-D- glucopyranose Beta-D-glucopyranose (Haworth) Beta-D-glucopyranose Alpha-D- glucopyranose (Haworth) ACTIVITY-5. Draw the Haworth formula for D-mannose and D-galactose. Label the alpha and beta anomer. CYCLIC FORMS OF FRUCTOSE D-fructose, a ketohexose sugar, can be presented using furanose and pyranose. Cyclic Fisher (furanose) 1 2OH Open chain Fisher Haworth formula (furanose) 1 CH2OH HOH,C- 1 2 F0 НО 3_H. ÇH2OH ÇH2OH но з—н 4 H- H но 2 H-4 HO- H- 5. OH 13 H-5 FOH 6 CH,OH 14 OH H. 6 CH2OH D-fructose Alpha form Alpha form Cyclic Fisher (pyranose) Haworth formula (pyranose) 1 HOH2C-2 3. 1 HO- CH2OH Но H. 5 он 2 H-4 HO- Но 4 OH 3 H-5 FHO- OH H-6 H Alpha form of D-fructose Alpha form of D-fructose ACTIVITY-6. Draw the Fisher and Haworth formula for beta-D-fructose (furanose and pyranose form). Label the beta furanose and beta pyranose.Two sugars differing in configuration at a single asymmetric carbon atom are known as epimers. D-mannose is a C-2 epimer of glucose (Structure I), while D-galactose is a C-4 epimer of glucose. Structure Il and IIl are H- -OH но- -H H OH HO H но- H HO H H -OH H- -OH HO OH H -OH H- -OH H OH HO. HO, OH II II Which of the following represents an aldopentose? OH H O HO O HO H но н HO H но- HO H HO H HO- H OH H OH H OH H OH OH HO Он of но" HO O OH он III IV These are chemical messengers that are secreted by endocrine glands and carried through the bloodstream to target tissues. prostaglandin deoxysugar glycoside hormones Which of the following is NOT correctly paired? cellulose: beta-1,4-glycosidic linkage amylose: alpha-1,4-glycosidic linkage chitosan: alpha-1,4-glycosidic linkage cellubiose: beta-1,4-glycosidic linkageD-Glucose, cyclic H (D-Glucopyranose) STEP 1 OH 0-H D-Glucopyranosyloxy anion STEP 2 Ring-opening same as D-Glucosyloxy anion STEP 3 |н
- . Draw the product in the following reactions; LIAIHĄ A но OH B H2SO4 OH 1. LAH 2. 2-propanone, H* C CH;OH, H* D 1. NACN 2. H2SO4, H20 NABH4 OH E F Ans . Show the ring closure scheme for the glucose molecule. AnsOH ОН Which monosaccharide has a greater heat of combustion, B-D-glucopyranose or B-D-allopyranose? Explain. но НО Но OH OH OH OH OH B-D-Glucopyranose B-D-AllopyranoseClassify the structures as being either an enantiomer, diastereomer or diastereomer/epimer of D-glucose. Structure A: CH H- -OH Structure B: но- H- H- OH Structure C: H- он H- -H D-Glucose: OH || CH CH CH он H- он но -H H- он но он но но- H- но H- OH OH но -- H- -H H -Ç-H Structure A: OH Structure B: OH Structure C: OH
- H,C- WWWM HC H2C Is the molecule above a mixed or a [ Select ] simple triglyceride? What reaction took place with the TAG above if one of the products is [ Select ] H3C. (CH2)12CH3Lactose is a disaccharide in which a glycosidic linkage connects the monosaccharides galactose and glucose. OH НО OH (a) Identify the glycosidic linkage and the acetal carbon in lactose. (b) What type of glycosidic linkage does lactose have (i.e., is it 1,1'-, 1,2'-, etc., and is it a or B)? (c) People who are lactose intolerant are deficient in the enzyme lactase, and therefore cannot efficiently break down the disaccharide into its monosaccharides. When lactose is treated with aqueous acid, however, this hydrolysis can take place, though relatively slowly. Draw the complete, detailed mechanism and the products of the acid-catalyzed hydrolysis of lactose. Но ОН НО ОН ОН Lactose(h) Identify B-D-altrose and a-D-altrose from the monosaccharides shown below. VI I CH2OH O. CH2OH II H V ОН, IV H III OH OH H (i) The monosaccharide below is a(n) (d-aldopentose, R-aldopentose, S- aldopentose, L-aldopentose, D-aldopentose).
- The following molecule has a glycosidic bond that is best described as HỌ – CH2 НО HỌ – CH2 HO OH O ОН alpha-1,4-glycosidic bond beta-1,6-glycosidic band alpha-1,6-glycosidic bond beta-1,4-glycosidic bond ОН OH OH.H2O1. Draw Haworth projections of B-D-arabinofuranose and a-L-mannopyranose. 2. Consider the structure of the disaccharide drawn at right: НО `CH2 В ОН (a) Give the names and D/L designation for the two monosaccharides linked together. H,C-O OHO „OH OH А: НО НО A В: ОН (b) In the structure, circle the anomeric carbon of each saccharide. (c) Is each saccharide present in its a or ß anomer? Specify both A and B (d) Would this disaccharide undergo mutarotation? Why or why not? (e) Would this disaccharide react with Tollens and/or Benedicts reagent? Why or why not? (f) There are two reasons this is very unlikely to be a naturally occurring disaccharide. What about its structure suggests this is true? Give both reasons.Draw the structure of a carbohydrate with four b-D-glucopyranosyl units connected by b(1®4) glycosidic linkages, with the second unit being connected via an a(1®6) glycosidic linkage by a side chain having two a-D-galactopyranosyl units connected by an a(1®4) glycosidic linkage.