2. Provide the Haworth projection for α-(D)-idopyranosyl-(1,1)-ẞ-(D)-glucofuranose (the Fischer projection for idose is provided below). HO -H H- -OH HO -H H -OH CH₂OH (D)-idose
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- 1. In the space provided, draw a Haworth projection for the alpha anomer of the following monosaccharide Fischer projection. H но CHO OH -H H- OH H- FOH CH₂OHA 2-ketohexose is reduced with NABH4 in CH3OH to form a mixture of D-galactitol and D-talitol. What is the structure of the 2-ketohexose?1. 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 Haworth projection for B-D-xylose The Products of the reaction of L-glucose with the following L-glucose [1] NH2NH4 [2] Ac2O,NaOAc [3] N2OCH3 Products of the reaction of D-threose with the following D-threose [1]NACN, HCI [2] H2, Pd-Baso, [3] H3O*m) Which pyranose ring (A, B, C, or D) in the tetrasaccharide below is derived from D-altrose? The Fischer projections for the four aldohexoses that make up this tetrasaccharide are shown below. B C D HOH CHO CHO CHO CHO HO+H HTOH Fонно н HOH HOH H-OH H-OH H-+-OH H-TOHHOH HOH H+OH HOHнтон нон CHOH CHOH CHOH CHOH De D-glue Dalose Datrone i NH Į HOH STEP 1 OH, HO- answer 1. Just add arrows and charges for steps 1, 2, and 3 in formation of this enamine з no arrows needed here OH н Н ЮН -OH STEP 3 :ÖH н H STEP 2 на это про за поч2) a-Draw the proper flat, Haworth form and most stable chair conformation for the B- anomer of L- glucopyranose b- Write the systematic name of this compound O: HO- НО—н НО H FOH HO-H -O- L-Gulose
- 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.4. Identify the component monosaccharides of each of the following compounds and describe the type of glycosidic linkage in each. Но он Но OH HO он Но- Но- (a) OH (c) CH,OHO. (b) CH2OHO Lon OH HO H ČHOH H OH ÓH ОННО Но н Н- НО он Н Н HO H OH оно н Н H. H Н ОН Н H н 아처 OH CH НО.
- What is the Fischer projection of the monosaccharide from which the following glycoside was prepared? НО. H- H Н CH.OH :0 -OH OH -OH CH₂OH HO- НО H ОН CH₂OH " H -H OH CH₂OH OH НО OH Н- Н- CH₂OH O H OH ОН CH₂OH Ш H— НО НО CH₂OH O OH H -H CH₂OH IVN-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 Ne7. Draw the Haworth structure for the following monosaccharides a. H НО H c=0 H + но - н 3 4 Н 5 - ОН - OH 애 CH₂OH 6 D-Mannose b. H 0 = с H - C - OH HO-C - H H - C - OH H - C - ОН CH₂OH Glucose