Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 22, Problem 38P
Interpretation Introduction
Interpretation:
On the basis of the information provided, the structure of stachyose is to be deduced.
Concept introduction:
Stachyose is a type of tetrasaccharide compound, which consists of two units of
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Researchers analysed a glycopeptide (a peptide carrying one or several oligosaccharide
groups) and determined both the sequence of the peptide and the sequence of the sugar molecule. The
latter was identified as a diholoside coupled to the peptide by an osidic bond. The systematic name
of this sugar is:
B-D-glucopyranosyl-(1→4)-ß-D-galactopyranose.
: Represent the chemical formula of this diholoside in a way that all oses are
Question 1
represented according to the Haworth convention. Apart from the furane and/or pyrane cycles all
atoms of this molecule must be given.
Treatment of a 258 mg sample of amylopectin by the methylation and hydrolysis procedure described yielded 12.4 mg of 2,3‑di‑O‑methylglucose. Determine what percentage of the glucose residues in amylopectin contained an (α1→6) branch. (Assume that the average molecular weight of a glucose residue in amylopectin is 162 g/mol and the molecular weight of 2,3‑di‑O‑methylglucose is 208 g/mol.)
(
α1→6) branched glucose residues: %
Emil Fischer synthesized l-gulose, an unusual aldohexose that reduces to give d-glucitol.Suggest a structure for this l sugar, and show how l-gulose gives the same alditol asd-glucose. (Hint: d-Glucitol has ¬CH2OH groups at both ends. Either of these primaryalcohol groups might have come from reduction of an aldehyde.)
Chapter 22 Solutions
Organic Chemistry
Ch. 22 - Prob. 1PPCh. 22 - Prob. 2PPCh. 22 - Prob. 3PPCh. 22 - Prob. 4PPCh. 22 - Prob. 5PPCh. 22 - Prob. 6PPCh. 22 - Prob. 7PPCh. 22 - Prob. 8PPCh. 22 - Practice Problem 22.9 What products would you...Ch. 22 - Prob. 10PP
Ch. 22 - Prob. 11PPCh. 22 - Prob. 12PPCh. 22 - Prob. 13PPCh. 22 - Prob. 14PPCh. 22 - Prob. 15PPCh. 22 - Prob. 16PPCh. 22 - Prob. 17PPCh. 22 - Prob. 18PPCh. 22 - Prob. 19PPCh. 22 - Prob. 20PCh. 22 - Prob. 21PCh. 22 - Prob. 22PCh. 22 - Prob. 23PCh. 22 - Prob. 24PCh. 22 - Prob. 25PCh. 22 - Prob. 26PCh. 22 - Prob. 27PCh. 22 - Prob. 28PCh. 22 - Prob. 29PCh. 22 - Prob. 30PCh. 22 - Prob. 31PCh. 22 - Prob. 32PCh. 22 - Prob. 33PCh. 22 - Prob. 34PCh. 22 - Prob. 35PCh. 22 - Prob. 36PCh. 22 - Prob. 37PCh. 22 - Prob. 38PCh. 22 - Arbutin, a compound that can be isolated from the...Ch. 22 - Prob. 40PCh. 22 - Prob. 41PCh. 22 - Prob. 42PCh. 22 - Prob. 43PCh. 22 - 22.44 The following reaction sequence represents...Ch. 22 - 22.45
The NMR data for the two anomers...Ch. 22 - Shikimic acid is a key biosynthetic intermediate...
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- d-(-)-Erythrose has the formula HOCH2¬CH(OH)¬CH(OH)¬CHO, and the d in its name implies that it can be degraded to d-(+)-glyceraldehyde. The (-) in its name implies that d-(-)-erythrose is optically active (levorotatory). When d-(-)-erythrose is reduced (using H2 and a nickel catalyst), it gives an optically inactive product of formula HOCH2¬CH(OH)¬CH(OH)¬CH2OH. Knowing the absolute configuration of d-(+)-glyceraldehyde (Section 5-14), determine the absolute configuration of d-(-)-erythrose.arrow_forwardWrite down the reactions: D-Glucose + HNO3 →arrow_forwardIdentify the organic functional group and reaction type for the following reaction. The reactant is a(n) - carboxylic acid hexose - Aldohexose - aldotetrose -deoxyhexose -carboxylic acid tetrose - ketohexose The product is a(n) - carboxylic acid tetrose - aldotetrose -alcohol hexose -aldohexose -carboxylic acid hexose - alcohol tetrose The reaction type is - hemiacetal formation -hydrolysis -oxidation( Benedict’s) -acetal formation -reduction( hydrogenation) - mutarotationarrow_forward
- Humans are able to digest amylose, but not cellulose. What structural features of these polysaccharides might be responsible for this? O amylose contains only beta glycosidic bonds where cellulose contains alpha glycosidic bonds O amylose contains only beta glycosidic bonds where cellulose contains alpha glycosidic bonds amylose contains only alpha peptide bonds where cellulose contains beta peptide bonds amylose contains only alpha glycosidic bonds where cellulose contains beta glycosidic bondsarrow_forwardIn addition to lactose, D-galactose and D-glucose can form different heterodisaccharides. Draw the structures (Haworth projections) of the (i) a-glucose-(1→1) -a-galactose and ii) a- glucose-(1→3)-?-galactose, two examples of heterodisaccharides that can form.arrow_forwardWhat structural feature is required for a carbohydrate to behave asreducing sugar?arrow_forward
- The carbonyl group in d-galactose may be isomerized from C1 to C2 by brief treatmentwith dilute base (by the enediol rearrangement, Section 23-7). The product is the C4epimer of fructose. Draw the furanose structure of the product.arrow_forwardDraw the structure of: (a) a polysaccharide formed by joining D-mannose units in 1→4-β- glycosidic linkages; (b) a polysaccharide formed by joining D-glucose units in 1→6-α- glycosidic linkages. The polysaccharide in (b) is dextran, a component of dental plaque.arrow_forwardHuman milk contains the oligosaccharide 2′-fucosyllactose (α-Lfucose-(1→2)-β-D-galactose-(1→4)-Dglucose), which may help protect the newborn from bacterial infections. Draw the structure of this oligosaccharide.arrow_forward
- Give the full biochemical name for an L-ketohexose with the following pattern of chiral centers: carbon #3 = L, carbon #4 = D.arrow_forward4. An iterative approach to oligosaccharide synthesis involves the use of protected glycals (sugars with C1-C2 double bond) as shown below. The product from the reaction of the first glycal with DMDO under anhydrous conditions is treated with another suitably-protected glycal to form a disaccharide glycal, and the process can be repeated to form a trisaccharide glycal, and so on... Crucial to the success of this approach is the stereoselective formation of the intermediate A in the scheme below. Draw the structure of A. DMDO CH₂Cl2 A OH ZnCl₂, THF OHarrow_forwardWhich of the following statements is not true about glucose? (i) It is an aldohexose. (ii) On heating with HI it forms n-hexanearrow_forward
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