trehalose is a disacharide that can be obtained from fungi sea uchins and insects. acid hydrolysis of trehalose yields only D-glucose. trehalose is hydrolysed by a-glucosidase but not b-glucosidase.methylation of trhalose followed by hydrolysis yield two molar equivalents of 2-3-4-6 -tetra-O-methyl-D-glucopyranose. deduce the structure of the trehalose using the experimental data

trehalose is a disacharide that can be obtained from fungi sea uchins and insects. acid hydrolysis of trehalose yields only D-glucose. trehalose is hydrolysed by a-glucosidase but not b-glucosidase.methylation of trhalose followed by hydrolysis yield two molar equivalents of 2-3-4-6 -tetra-O-methyl-D-glucopyranose. deduce the structure of the trehalose using the experimental data

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter28: Biomolecules: Nucleic Acids

Section28.SE: Something Extra

Problem 20MP: One of the steps in the biosynthesis of uridine monophosphate is the reaction of aspartate with...

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3 Trehalose is a disaccharide that can be obtained from fungi, sea urchins and insects. Acid hydrolysis of trehalose yields only D-glucose. Trehalose is hydrolysed by α-glucosidase and not by β-glucosidase enzymes. Methylation of trehalose followed by hydrolysis yields two molar equivalents of2,3,4,6-tetra-O-methyl-D-glucopyranose.From the following experimental data, deduce the structure of trehalose.What will be the effect of trehalose on Fehling’s solution?
1. Trehalose is a disaccharide that can be obtained from fungi, sea urchins and insects. Acid hydrolysis of trehalose yields only D-glucose. Trehalose is hydrolysed by α-glucosidase and not by β-glucosidase enzymes. Methylation of trehalose followed by hydrolysis yields two molar equivalents of 2,3,4,6-tetra-O-methyl-D-glucopyranose.From the following experimental data, deduce the structure of trehalose.What will be the effect of trehalose on Fehling’s solution? 2.Suggest a test you will use to show that a given food substance contains protein
Trehalose, C12H22O11, is a nonreducing sugar that is only 45% as sweet as sugar. When hydrolyzed by aqueous acid or the enzyme maltase, it formsonly d-glucose. When it is treated with excess methyl iodide in the presence of Ag2O and then hydrolyzed with water under acidic conditions, only2,3,4,6-tetra-O-methyl-d-glucose is formed. Draw the structure of trehalose.
Prove that gentiobiose forms osazone and can undergo mutarotation can be hyrolyzed by Emulsin β-glycosidase forms these hydrolysis products following permethylation: 2,3,4,6-tetra-O-methyl-D-glucose and 2,3,4-tri-O-methyl-D-glucose
Naturally occurring compounds called cyanogenic glycosides, such as lotaustralin, release hydrogen cyanide, HCN, when treated with aqueous acid. The reaction occurs by hydrolysis of the acetal linkage to form a cyanohydrin, which then expels HCN and gives a carbonyl compound. (a) Show the mechanism of the acetal hydrolysis and the structure of the cyanohydrin that results. (b) Propose a mechanism for the loss of HCN, and show the structure of the carbonyl compound that forms.
Following is a retrosynthesis for the coronary vasodilator ganglefene. (a) Propose a synthesis for ganglefene from 4-hydroxybenzoic acid and 3-methyl-3-buten-2-one. (b) Is ganglefene chiral? If so, which of the possible stereoisomers are formed in this synthesis?
One of the later steps in glucose biosynthesis is the isomerization of fructose 6-phosphate to glucose 6-phosphate. Propose a mechanism, using acid or base catalysis as needed.
(S)-Glutamic acid is one of the 20 amino acid building blocks of polypeptides and proteins (Chapter 27). Propose a mechanism for the following conversion.
The first step in the metabolism of glycerol, formed by digestion of fats, is phosphorylation of the pro-Râ€”CH2OH group by reaction with adenosine triphosphate (ATP) to give the corresponding glycerol phosphate plus adenosine diphosphate (ADP). Show the stereochemistry of the product.
One of the steps in the biosynthesis of uridine monophosphate is the reaction of aspartate with carbamoyl phosphate to give carbamoyl aspartate followed by cyclization to form dihydroorotate. Propose mechanisms for both steps.
An optically active D-aldopentose (A) produced an optically inactive alditol (B) upon treatment with H2/Pt. When the aldopentose (A) was subjected to a Ruff degradation, D-aldotetrose (C) was generated. The aldotetrose (C) gave an optically active aldaric acid (D) upon oxidation with HNO3. D-aldopentose (A) can be prepared from D-threose by a Killani Fischer synthesis. Propose structure of A through D.
Draw a mechanism for the conversion of glucose from its aldehyde form to its hemiacetal form and then to its methyl glycoside (acetal) form under acidic conditions. Show all bond breaking and bond forming steps; show all intermediates.