On the templates, draw a Haworth projection of the a-isomer and ß-isomer of the sugar shown. (b) Draw the chair form of the a-isomer. H HO HO H CHO -OH (b) chair form: H -H -OH CH₂OH a-isomer A B-isomer
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- (d) Draw the structure of the expected product when monosaccharide B undergo mutarotation upon dissolving in water in the presence of Tollens reagent (AGNO3, NHẠOH). он OH O. OH OH OH monosaccharide BTwo 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 linkage5. Provide suitable responses for questions (a) – (). 6 CH2OH 4 OH OH 3 OH (a) What is the relative configuration of the above monosaccharide? (b) Which labeled carbon is the anomeric carbon? (c) Trace and identify the acetal in the above monosaccharide. (d) Draw the hemiacetal that results from above acetal. (e) Draw the open chain equivalent of the sugar in part (d). (f) Classify the monosaccharide below as a D-sugar or an L-sugar. H. OH O. OH CH,OH OH OH
- Of the four structures shown here in Fischer projections, indicate the relationships between (a) and (b), and between (c) and (d)? CHO CHO нтон нотн CH₂OH (a) CH₂OH (b) ÇO₂H H-OH -OH -он но- HO- CO₂H (c) II HO-H ÇO₂H of A. Both pairs are enantiomers O B. Both pairs are identical C. (a) and (b) are enantiomers, (c) and (d) are identical D. (a) and (b) are identical, (c) and (d) are enantiomers II CO₂H (d)Draw all the possible stereoisomerism for following structures. Label the chiral centre with an asterisk (*) if any. (a) CНICOОH)(NH)CH-COOH (b) (CH3)2C=C(COOH)CH(NO2)CH3Classify 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
- Draw the Haworth or Chair Haworth structures of the following disaccharides: (a) α-D-glucopyranosyl-(1,4)-β, D-galactopyranose (b) β,D-galactopyranosyl-(1,4)-α-D-glucopyranose (c) β-D-glucopyranosyl-(1,4)-α,D-galactopyranose. Identify all anomeric carbons and hemiacetal, acetal, hemiketal, and ketal linkages.5. Consider the following pairs of structures. Identify the relationship between them (enantiomers, diastereomers, or identical compounds. HOH2C H OH H OH HO H Br H3C Н H H₂CH₂C CI Br H CHO CH3 I CH3 OH OHC Н H OH H OH Bell!! H3C, HO H Н.С H CH₂CH3 CH3 CI HỌ,H CH₂OH BrBe sure to answer all parts. [1] classify the compound as a D or L monosaccharide; [2] draw the the enantiomer of the compound. H. но- H. -OH но- -H ČH,OH [1] (select) (select) L D
- 2. How is each compound related to the simple sugar D-erythrose? Is it an enantiomer, diastereomer or identical? ОНС HO HOH C НО НОН С A с он E ОНС. CH₂OH OH CHO ОН CHO OH он OH D-erythrose CH₂OH ОНС НО HOH2C HO HOH C B D OH CH2OH ОН F CHO ОН CHO онProvide suitable responses for questions (a) –(j).| 6 CH2OH 4 ОН OH OH 2.(a) assign R or S configuration to each chiral center, (b) Which compound are enantiomers? (c) Which compounds are diastereomers?