1. Draw D-N-acetylglucosamine pyranose (NAG) as a Haworth projection with the beta- anomeric configuration: CHO H- NHẠC HO H H- OH H- -OH CH₂OH
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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 B1. Draw/lable out 2 chiral centers in ephedrine. 2. Lable out the chiral center in epinephrine.N-NHPH CHO CH2OH H- C=N-NHPH Но- -H- 3 equiv Но- -H- 3 equiv Но- PHNHNH2 PHNHNH, H- H- OH H- -O- H- H- -HO- H- -HO- ČH2OH ČH2OH ČH2OH D-glucose osazone D-fructose + NH3 + PHNH2 + 2 H20 The final step in the formation of the osazone from glucose is the reaction of the keto imine with 2 equivalents of phenylhydrazine to yield the osazone plus ammonia. This reaction involves the following intermediate steps: 1. Addition of phenylhydrazine to the imine and proton transfer to yield intermediate 1; 2. Elimination of ammonia to yield phenylhydrazone 2; 3. Addition of phenylhydrazine to the ketone to yield tetrahedral intermediate 3; 4. Proton transfer yields carbinolamine 4; 5. Elimination of water yields the final product osazone. Write out the mechanism on a separate sh of paper and then draw the structure of tetrahedral intermediate 3. NH НО- -H H- -ОН H- -ОН ОН Glucose keto imine Previous Ne
- Identify the relationship between the following structures. НО. CH3 CI diastereomers O enantiomers OH the same compound different compoundsIs this relationship between the pair an enantiomer or diastereomer? why?Identify the type of bond illustrated below: CHOH CHOH CHOH H OH H OH H OH H H OH OH O alpha-glycosidic bond O beta-glycocidic bond O beta-glycosidic bond O alpha glycocidic bond
- Identify the type of glycosidic bond in the following disaccharide. CH,OH H H ОН Н CH2 H H H ОН Н HO ОН H. ОН HO H H OH O B-1,4-glycosidic bond O a-1,4-glycosidic bond O B-1,6-glycosidic bond O a-1,6-glycosidic bond16. Glycoprotein A of human erythrocyte is O-glycosylated. Draw the chemical structure of the O- linked oligosaccharide shown below. Gal-B(1->3) -GalNAc-a-Ser/Thr 12,3 NeuNAC-a NeuNAC N-acetylneuraminic acid HO HO HO OH COO OHFollowing is the Haworth structure of a disaccharide. Identify the type of glycosidic bond in this disaccharide. CH₂OH H HO H OH H H OH H H a-1,6-glycosidic bond O a,B-1,2-glycosidic bond O B-1,4-glycosidic bond O a-1,4-glycosidic bond CH₂OH H OH H H OH H OH B a hp