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 a-glucosidase and not by B- glucosidase enzymes. Methylation of trehalose followed by hydrolysis yields two molar equivalents of 2,34,6-tetra-0-methyl-D-glucopyranose. (a) From the following experimental data, deduce the structure of trehalose. (b) What will be the effect of trehalose on Fehling's solution?

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 a-glucosidase and not by B- glucosidase enzymes. Methylation of trehalose followed by hydrolysis yields two molar equivalents of 2,34,6-tetra-0-methyl-D-glucopyranose. (a) From the following experimental data, deduce the structure of trehalose. (b) What will be the effect of trehalose on Fehling's solution?

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter25: Biomolecules: Carbohydrates

Section25.SE: Something Extra

Problem 60AP

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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 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, 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.
Treatment with NaBH 4 converts aldose U into an optically inactive (meso) alditol V. Ruff degradation ofU gives W, whose alditol is optically inactive. Ruff degradation of W forms D-glyceraldehyde, thesimplest aldose. Upon Kiliani-Fischer synthesis, U is converted to two aldoses, X and Y. X is oxidized toan optically active aldaric acid Z. Y is oxidized to an optically inactive aldaric acid. Draw the structuresof D-glyceraldehyde, V, W, X, Y, and Z. Structure of compound U is shown below.
An oligosaccharide isolated from an organism is found tocontain two glucose residues and one galactose residue.Exhaustive methylation followed by hydrolysis producedtwo glucoses with methoxy groups at positions 2, 3,and 6 and galactose with methoxy groups at positions2, 3, 4, and 6. What is the structure of the originaloligosaccharide?
An aldopentose "O", is oxidized with HNO3 to a diacid "P" which is optically active. The compound "O", is also degraded to an aldotetrose "Q" which undergoes another oxidation to an optically inactive diacid "R". Assuming that "O" has the configuration D-(4R); what are the structures of "O" to "R"?
Predict the products obtained when d-galactose reacts with each reagent. (f) excess Ac2O and pyridine (g) excess CH3 I, Ag2O
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.
Predict the products obtained when d-galactose reacts with each reagent.(a) Br2 and H2O (b) NaOH, H2O (c) CH3OH, H + (d) Ag(NH3) 2+ -OH(e) H2, Ni (f) excess Ac2O and pyridine (g) excess CH3 I, Ag2O (h) NaBH4(i) Br2, H2O, then H2O2 and Fe2(SO4)3 (j) (1) KCN/HCN; (2) H2, Pd/BaSO4; (3) H3O! (k) excess HIO42
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
Treatment of -D-glucose with methanol in the presence of an acid catalyst converts it into a mixture of two compounds called methyl glucosides (Section 25.3A). In these representations, the six-membered rings are drawn as planar hexagons. (a) Propose a mechanism for this conversion and account for the fact that only the OH on carbon 1 is transformed into an OCH3 group. (b) Draw the more stable chair conformation for each product. (c) Which of the two products has the chair conformation of greater stability? Explain.