Fundamentals of General, Organic, and Biological Chemistry (8th Edition)
8th Edition
ISBN: 9780134015187
Author: John E. McMurry, David S. Ballantine, Carl A. Hoeger, Virginia E. Peterson
Publisher: PEARSON
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Textbook Question
Chapter 20.5, Problem 20.14P
Draw the structure of the α and β anomers that result from the reaction of methanol and ribose. Are these compounds acetals or hemiacetals?
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Which of the following is the correct statement for the a anomer and B anomer of D-arabinose?
O They contain axial or equatorial carbonyl groups.
They have different configurations around only one carbon atom
They are two unstable ring structures that are mirror images.
O They contain different numbers of hydroxyl groups.
Draw the structure of each of the following compounds:
a. a polysaccharide formed by joining D-glucosamine in 1-→6-a-glycosidic linkages
b. a disaccharide formed by joining D-mannose and D-glucose in a 1-4-B-glycosidic linkage using mannose's anomeric
carbon
c. an a-N-glycoside formed from D-arabinose and CgH;CHNH2
d. a ribonucleoside formed from D-ribose and thymine
Draw the keto or enol tautomer for each of the following compounds when they were
treated with traces of acids or bases.
CH3
OH
(1)
?
H
H
(2)
CH₂CH₂
C=C₂
CH3
?
Chapter 20 Solutions
Fundamentals of General, Organic, and Biological Chemistry (8th Edition)
Ch. 20.1 - Classify the following monosaccharides as an...Ch. 20.1 - Prob. 20.2PCh. 20.2 - Prob. 20.3PCh. 20.2 - Prob. 20.4PCh. 20.2 - Prob. 20.6PCh. 20.3 - D-Talose, a constituent of certain antibiotics,...Ch. 20.3 - Prob. 20.8PCh. 20.3 - Draw the structure that completes the mutarotation...Ch. 20.4 - Prob. 20.10KCPCh. 20.4 - Prob. 20.11P
Ch. 20.4 - Prob. 20.12PCh. 20.4 - Prob. 20.13PCh. 20.4 - Prob. 20.1CIAPCh. 20.4 - Prob. 20.2CIAPCh. 20.4 - All cells in your body contain glycoproteins...Ch. 20.5 - Draw the structure of the and anomers that...Ch. 20.6 - Prob. 20.15PCh. 20.6 - Prob. 20.16PCh. 20.6 - Prob. 20.17KCPCh. 20.7 - Prob. 20.4CIAPCh. 20.7 - Prob. 20.5CIAPCh. 20.7 - Prob. 20.6CIAPCh. 20.7 - Prob. 20.7CIAPCh. 20.7 - Prob. 20.18PCh. 20.7 - Prob. 20.19PCh. 20.7 - Prob. 20.8CIAPCh. 20.7 - Prob. 20.9CIAPCh. 20.7 - Prob. 20.10CIAPCh. 20 - During the digestion of starch from potatoes, the...Ch. 20 - Prob. 20.21UKCCh. 20 - Consider the trisaccharide A, B, C shown in...Ch. 20 - Hydrolysis of both glycosidic bonds in the...Ch. 20 - Prob. 20.24UKCCh. 20 - Are one or more of the disaccharides maltose,...Ch. 20 - Prob. 20.26UKCCh. 20 - Prob. 20.27UKCCh. 20 - Prob. 20.28APCh. 20 - What is the family-name ending for a sugar?Ch. 20 - Prob. 20.30APCh. 20 - Classify the four carbohydrates (a)(d) by...Ch. 20 - Prob. 20.32APCh. 20 - How many chiral carbon atoms are there in each of...Ch. 20 - Prob. 20.34APCh. 20 - Prob. 20.35APCh. 20 - Name four important monosaccharides and tell where...Ch. 20 - Prob. 20.37APCh. 20 - Prob. 20.38APCh. 20 - What is the structural relationship between...Ch. 20 - Prob. 20.40APCh. 20 - In Section 15.6, you saw that aldehydes react with...Ch. 20 - Sucrose and D-glucose rotate plane-polarized light...Ch. 20 - Prob. 20.43APCh. 20 - Prob. 20.44APCh. 20 - Prob. 20.45APCh. 20 - What is mutarotation? Do all chiral molecules do...Ch. 20 - What are anomers, and how do the anomers of a...Ch. 20 - What is the structural difference between the ...Ch. 20 - D-Gulose, an aldohexose isomer of glucose, has the...Ch. 20 - Prob. 20.50APCh. 20 - In its open-chain form, D-altrose has the...Ch. 20 - Prob. 20.52APCh. 20 - Prob. 20.53APCh. 20 - Prob. 20.54APCh. 20 - Prob. 20.55APCh. 20 - What is the structural difference between a...Ch. 20 - What are glycosides, and how can they be formed?Ch. 20 - Prob. 20.58APCh. 20 - Prob. 20.59APCh. 20 - Give the names of three important disaccharides....Ch. 20 - Lactose and maltose are reducing disaccharides,...Ch. 20 - Amylose (a form of starch) and cellulose are both...Ch. 20 - Prob. 20.63APCh. 20 - Prob. 20.64APCh. 20 - Prob. 20.65APCh. 20 - Gentiobiose, a rare disaccharide found in saffron,...Ch. 20 - Prob. 20.67APCh. 20 - Prob. 20.68APCh. 20 - Prob. 20.69APCh. 20 - Amylopectin (a form of starch) and glycogen are...Ch. 20 - What is the physiological purpose of starch in a...Ch. 20 - Prob. 20.72APCh. 20 - Prob. 20.73APCh. 20 - Prob. 20.74CPCh. 20 - Prob. 20.75CPCh. 20 - Prob. 20.76CPCh. 20 - Prob. 20.77CPCh. 20 - Prob. 20.78CPCh. 20 - Write the open-chain structure of the only...Ch. 20 - Prob. 20.80CPCh. 20 - Prob. 20.81CPCh. 20 - When a person cannot digest galactose, its reduced...Ch. 20 - Describe the differences between mono-, di-, and...Ch. 20 - Prob. 20.84CPCh. 20 - Prob. 20.85CPCh. 20 - Many people who are lactose intolerant can eat...Ch. 20 - Prob. 20.87GPCh. 20 - Prob. 20.88GPCh. 20 - Prob. 20.89GP
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Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, biochemistry and related others by exploring similar questions and additional content below.Similar questions
- Draw the structure of: The polysaccharide in (b) is dextran, a component of dental plaque. Here b: (b) a polysaccharide formed by joining D-glucose units in 1→6-α-glycosidic linkagesarrow_forwardD-Talose is a C2 epimer of D-galactose. Using the Fischer projection structure, draw the product of reaction ofD-talose with the given reagent or enzyme and write the systematic name of the product. 1. 2,4-DNP 2. Reaction with aminotransferase and then acetyltransferase at C4arrow_forwardLook up structures of D-xylose and asparagine and draw a structure of Xyl(beta1->3)Xyl connected to asparagine's side chain via the remaining anomeric carbon (use alfa anomer).arrow_forward
- Draw both possible disaccharides of D-psicose and D-mannose that are joined by an α(1→4) glycosidic linkage. Are either of them now a reducing sugar?arrow_forwardSucrose, a major product of photosynthesis in green leaves, is synthesized by a battery of enzymes. The substrates for sucrose synthesis, D -glucose and D fructose, are a mixture of α and β anomers as well as acyclic compounds in solution. Nonetheless, sucrose consists of α - D -glucose linked by its carbon-1 atom to the carbon-2 atom of βD -fructose. How can the specificity of sucrose be explained in light of the potential substrates?arrow_forwardTrehalose, also known as mycose, is a disaccharide found in certain mushrooms. It is composed of two a-D-glucose linked in a aa(1à1) glycosidic bond. Using Haworth projection, draw the structure of trehalose. Indicate whether it is reducing or non-reducing.arrow_forward
- Why is alpha (a) the predominant anomeric form of mannose? A. The alpha-anomer is more unstable because of the presence of more axial substituents B. The beta-anomer is more unstable because of the delta-2 effect of steric repulsions between the lone pairs of the equatorial OH at C1 and the axial OH at C2 C. The beta-anomer is more unstable because of the steric repulsions between the lone pairs of the equatorial OH at C1 and C2 D. Although the alpha-anomer has more axial OH, the instability factors created by one is cancelled by the other. E. The alpha-anomer creates a more open structure than the beta-anomer.arrow_forwardDraw a Fischer projection of L-fucose and L-hexose. What are the similarities in their structure?arrow_forwardImagine a trisaccharide that has D-Altrose, D-Gulose, and D-Ribose. D-Altrose is bonded to D-Gulose in an α(1→4) glycosidic bond and D-Ribose is bonded to D-Altrose in an α(1→6) glycosidic bond. Draw the imaginary trisaccharide using Haworth projection with the appropriate representation of each monosaccharide.arrow_forward
- Alginic acid, isolated from seaweed and used as athickening agent for ice cream and other foods, is apolymer of d-mannuronic acid with b(1,4) glycosidiclinkages.a. Draw the structure of alginic acid.b. Why does this substance act as a thickening agent?arrow_forwardThe tripeptide Glu-Pro-Arg (EPR) which is a product of Lactobacillus casei fermentation of milk was found to have potent blood pressure-lowering properties. Draw the structure of the tripeptide and give its systematic name. Then show its titration profile and determine its isoelectric pH.arrow_forwardDraw the two possible Haworth structures (both alpha and beta anomers) for the following monosaccharides and give their corresponding systematic names. Show and explain the stepwise processarrow_forward
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