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
Answer the following questions regarding the trisaccharide composed of a glucose, mannose
and galactose
a) What is the configuration on the anomeric carbon for the each of the sugars
b) Which sugar end(s) are reducing?
c) What is the numbering on the linkage connecting the glucose to the mannose?
d) What is the numbering on the linkage connecting the mannose to the galactose?
OH
CH,OH
Galactose
но.
но,
CH,OH
но
но.
он
Glucose
но.
он
Mannose
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
- D-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_forwardDraw 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 ?arrow_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 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_forwardDraw 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_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
- Sucrose, 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_forwardDraw a Fischer projection of L-fucose and L-hexose. What are the similarities in their structure?arrow_forwardWhy 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_forward
- Imagine 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_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_forwardAlginic 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_forward
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