Concept explainers
Interpretation:
The number of chiral centers in the open chain form of
Concept Introduction:
The carbon atom which is bonded to four different groups is known as stereogenic or chiral center.
Sodium borohydride
The structural representation of sugar molecule in cyclic form is known as Haworth projection. Sugar molecule that has six-membered-ring is known as pyranose and sugar molecule that has five-membered-ring is called furanose.
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CAREY: ORGANIC CHEMISTRY
- The anticoagulant heparin is a polysaccharide that contains alternating residues of -D- glucuronic acid-6- sulfate and N-sulfo-D-glucosamine-6sulfate connected by (1 B 4)- glycosidic linkages. Draw a part of heparin that shows one each of the two residues.arrow_forwardConsider the structure of raffinose, a trisaccharide found in sugar beets and a number of higher plants. HO CH,OH Но- OH OCH, Но Но OH НОСН Но CH,OH ÓH raffinose (a) Classify raffinose as a reducing or nonreducing sugar, and tell how you know. (b) Identify the glycoside linkages in raffinose, and clas- sify each as either a or B. (c) Name the monosaccharides formed when raffinose is hydrolyzed in aqueous acid. (d) What products are formed when raffinose is treated with dimethyl sulfate in NaOH, and then with aqueous acid and heat?arrow_forwardRegarding 4-O- (α-D-psychofuranosyl) -β-D-allopyranose. Please indicate the RIGHT alternative: (a) The disaccharide reacts with CH3OH in an acid medium to form a glycoside that cannot be oxidized with HNO3. (b) It is a reducing disaccharide only in basic medium. (c) In the structure there is only one glycosidic bond that is of the type β 1-O-4 ' (d) The hydrolysis products of this disaccharide do not show mutarrotation. (e) The disaccharide structure contains two six-membered rings.arrow_forward
- 5. 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 OHarrow_forwardLactose 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 Lactosearrow_forwardDraw the structures (using chair conformations of pyranoses) of the following disaccharides.(a) 4-O-(a-d-glucopyranosyl)-d-galactopyranose(arrow_forward
- (g) Using appropriate prefixes/infixes/suffixes (ketohentese, aldahentase, etc.), classify each of the monosaccharides shown below. СНО CH2OH O: HOI но ОН OH HO H. CH2OH CH2OH I II (h) Identify B-D-altrose and oa-D-altrose from the monosaccharides shown below. CH2OH CH2OH CH2OH CH2OH O. ОН OH OH OH OH OH ОН OH OH OH ОН OH OH OH OH OH I II III IV | (i) Identify B-D-altrose and oa-D-altrose from the monosaccharides shown below. VI I CH2OH CH2OH II V OH III ОН IV H OH Harrow_forward4. 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 ОНarrow_forwardWhich D-aldopentoses are reduced to optically inactive alditols using NaBH4, CH3OH?arrow_forward
- Draw a Haworth projection for the disaccharide gentibiose, given the following information:(a) It is a dimer of glucose.(b) The glycosidic linkage is B(1 -> 6).(c) The anomeric carbon not involved in the glycosidic linkage isin the B configuration.arrow_forward(g) Using appropriate prefixes/infixes/suffixes (ketoheptose, aldoheptose, etc.), classify each of the monosaccharides shown below. CHO CH2OH Но IH но- HO- HO- HO H. CH2OH CH2OH I II (h) Identify B-D-altrose and a-D-altrose from the monosaccharides shown below. CH2OH CH2OH CH2OH CH2OH OH OH OH ОН OH ОН ОН OH OH OH OH OH OH OH OH OH I II II IV (i) Identify B-D-altrose and a-D-altrose from the monosaccharides shown below. VI I CH2OH O CH2OH II H V ОН, III IV OH OH Harrow_forwardCompound A is a D-aldopentose that can be oxidized to an optically inactive aldaric acid B. On Kiliani-Fischer chain extension, A is converted into C and D; C can be oxidized to an optically active aldaric acid E, but D is oxidized to an optically inactive aldaric acid F. What is the structure of compound F? • Use the wedge/hash bond tools to indicate stereochemistry where it exists. You do not have to explicitly draw H atoms. If a group is achiral, do not use wedged or hashed bonds on it. • Show stereochemistry in a meso compound. • Do not include lone pairs in your answer. They will not be considered in the grading.arrow_forward
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