Identify the type of glycosidic bond for each of the following sugars. Choose from a-(1-2), a- (1-3), a-(1-4), a-(1-5), a-(1-6), B-(1-2), ß-(1-3), ß-(1-4), ẞ-(1-5), ß-(1-6), or a,ẞ- (1+2) CH₂OH 0 HO H H OH H H H OH O a-(1-6) glycosidic bond OB-(1-5) glycosidic bond OB-(1-6) glycosidic bond Oa-(1-5) glycosidic bond CH₂ HO H H OH H H 0 H HP OH
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- The following molecule has a glycosidic bond that is best described as HỌ— CH2 НО HO-CH2 НО OH O OH alpha-1,4-glycosidic bond beta-1,6-glycosidic bond alpha-1,6-glycosidic bond beta-1,4-glycosidic bond OH OH OH. H2OGentiobose is found in saffron. Gentribose contains two glucose molecules linked by a beta (1 - 6) glycosidic bond. Describe how to draw the glycosidic linkage in this structuree) 4) Identify the type of glycosidic bond for each of the following sugars. Choose from a-(1→2), a-(1-3), a-(1-4), a-(1-5), a-(1-6), B-(1-2), B-(1-3), B-(1-4), B (15), B-(1-6), or a,ß-(142) a) c) HO b) Н H CH OH а H OH N H ОН Н CH₂OH OH H CI CH₂OH N HO HO H Н ОН HO Н H HO H H CH OH хох OH H H 0 H CH₂OH CH₂ OH H НО CH2OH H HO Н O HO Н HO H 0 H b. HO Н H Н d) CH₂OH НО H - 0 Н H OH НО CH OH H HO Н И H ОН 9 HOCH₂ OH H Н ОН CH₂OH 5 H OH H H Но Н CI H N 5. Determine the number of chiral carbons in the following structures, and how many stereoisomers are possible. НО HO H H CH OH
- Following 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 hpConsider the molecular structure of a disaccharide. _OH OH H H ма OH H ону Н OH Н OH Identify the type of glycosidic linkage in the disaccharide. O a (1 - 4) a (1 - 2) → 4) OB (I - OB (1 - 2) Label the structures to show the monosaccharide units produced by hydrolysis of the disaccharide. C Н OH Н OH ОН Answer Bank CH₂OH HThe 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.H2O
- Consider the following Haworth structure of a disaccharide and identify the type of glycosidic bond in it. a-1,6-glycosidic bond a-1,4-glycosidic bond a,ß-1,2-glycosidic bond O B-1,4-glycosidic bond H HO HOCH2 H CH₂OH H OH H H OH H OH OH H H CH₂OHPart 3 of 3 Modify the structure of lactulose to show the monosaccharide products that form from hydrolysis. You may draw the structures in any arrangement that you like, so long as they aren't touching. он H сн, он :☐ Он × 5 H H HO снон Сн, он H Он Н д- Н Н OH НN-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
- OH НО HO OH НО Но OH ОН ОН OH What are the monosachharides that make up this trisaccharide? O a-D-glucopyranose, a-D-galactopyranose, a-D-fructofuranose a-D-glucopyranose, a-D-galactopyranose, B-D-fructofuranose a-D-glucopyranose, a-D-glucopyranose, B-D-fructofuranose a-D-galactopyranose, a-D-glucopyranose, a -D-fructofuranoseIdentify 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 bondPlease draw a tetrasaccharide. The cyclic monosaccharide needed is pictured below. Step 1: Connect 3 glucose units through a (1-4) glycoside bonds Step 2: Connect the 4th glucose unit to the second glucose unit through a a (1-3) glycoside bond glucose CH₂OH OH OH OH OH