Concept explainers
Interpretation:
The pyranose form of β-anomer of D-talose is to be drawn. The ring substituents are to be identified as axial or equatorial.
Concept introduction:
The pyranose form is a cyclic hemiacetal form with a six membered ring formed by the nucleophilic addition of the –OH group on C5 to the C1 carbonyl group. The furanose form is a cyclic hemiacetal form with a five membered ring formed by the nucleophilic addition of the –OH group on C5 to the C2 carbonyl group.
The orientation of –OH group differs in α- and β- anomers. In α- anomer the OH on C1 is cis to the –OH at the lowest chirality center in Fischer projection, while in β- anomer the –OH on C1 is trans to the –OH at the lowest chirality center in Fischer projection.
D sugars have the –O- at C adjacent to CH2OH on the right in the uncoiled form while L sugars have the -O- at C adjacent to CH2OH on the left.
To draw:
The pyranose form of β-anomer of D-talose and to identify the ring substituents as axial or equatorial.
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Chapter 25 Solutions
Organic Chemistry
- Lactose 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_forwardGive an 1-2 sentence explanation each of the effects/reactions in iodine test in Glucose, fructose, Galactose, Sucrose, Lactose, Maltose, and starcharrow_forwardCellulose, the major structural material of wood and plants, consists of a chain of B-D-glucose molecules connected by B-1,4-glycosidic bonds. In comparison, the amylose component of starch consists of a-D-glucose molecules connected by a-1,4-glycosidic bonds. Identify the following structures, denoted A and B, as the structures of cellulose or amylose. A В 0 Н CH2OH H . н Н OH H Н CH₂OH 0 Н ОН Н ОН Н Н ОН О О Н Н CH₂OH -0 Н OH H Н CH₂OH 0 Н ОН Н ОН Н Н ОН OB is the structure of cellulose, while A is the structure of amylose. O A and B both represent the structure of amylose. O A is the structure of cellulose, while B is the structure of amylose. O A and B both represent the structure of cellulose. Н 0 0 H Н CH₂OH до Н ОН Н Н H OH CH₂OH 0 Н ОН Н Н Н ОН Н О Н H CH₂OH -о Н ОН Н Н ОН CH₂OH 0 H OH HA Н ОН Н H 0arrow_forward
- Contrast the structure of glycogen and chitin. Drag the appropriate items to their respective rows. Glycogen Chitin Monomers connect by B-1,4-glycosidic linkages Monomers connect by alpha-1,4-glycosidic linkages Polymers interact with one another via hydrogen bonds Consists of modified glucose residues (NAG) Contains branches arising from alpha-1,6-glycosidic linkages Consists of glucose residuesarrow_forwardDraw 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*arrow_forwardGive the correct numbering of the rings. How is this structure different from sucrose? екен. СТ 11 11 ко НО НО Н- Н HO НО Н H Н CHOU 11 onl " 11/1 Is the polymer below alpha or beta anomer? Number the carbons 11 On 0. ОН И CH OH !! 011 H он H OIL н 0 C-H H 0-0 С-Н H -Н What type of reaction is occurring? Oxidation / reduction? What is the reagent used? () CH-CI OH OLL -OH CH₂OH H -Н -OH -ОН CH OH What reagent is used to form the product? CH OH H OLI H 11 ОН II H Н- HO -Н НО H CH OH Н- H- OH OH CH OH СООН НО -H НО -Н -OH OH CH OH Identify the alpha and beta anomer. Which is reducing/ non-reducing sugar? H.C-OH O OH H Н Кон н Н H OH 0 Сн HOH HO но- -H HOH CH OH H -Н H co Write the cyclic forms of D-galactose. Why is it a D sugar? Will the hydroxy group at the 4th position be up or down? н-он по-п OH H-- OL СИОН 11 OH ift. Identify these structures. Which is an aldose, ketose, D or Letc CHINE H 11 11 H.C OH O OH ΤΗ H 11 OH H M H OH CIL-OH C-0 но-н HOH 1----Ou HT CH-OH What is the term…arrow_forward
- Fisher Projection, Haworth representation and Pyranose/furanose Ring structures of α-D-xylulose 2. Fisher Projection and Pyranose/furanose Ring structures of β-D-talopyranosearrow_forward14. (a) Identify the acetal and the ketal group in the following disaccharide. (b) Decide whether the compound is a non-reducing or reducing sugar. OH НО HƠ HO Н HO Н НО HO 15. (a) Identify the glycosidic bond in the following disaccharide. (b) Decide whether the compound is a non-reducing or reducing sugar. (c) Polysaccharide units are usually bonded together with a or B 1, 6 or 1, 4 linkages. What linkage is used in the disaccharide shown below? s) НО НО НО HO НО -OH OH -H OH CH2OH 16. Draw the structure for 1,4-B-D-galactopyranosyl-D-glucose. ( но- 17. Assign an R/S designation to each chirality center in the following compound: ( CHO НО -OHarrow_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_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_forwardGentiobose 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 structurearrow_forwardDetermine the branch points and reducing ends of amylopectin. A 0.5g sample of amylopectin was analyzed to determine the fraction of the total glucose residues that are branch points in the structure. The sample was methylated and then digested, yielding 50 μmol of 2,3-methylglucose and 0.4 μmol of 1,2,3,6-tetramethyl glucose. (MWglucose = 162 g/mol, minus H2O) What fraction of the total residues are branch points? How many reducing ends does the amylopectin have?arrow_forward
- Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage Learning