EBK ESSENTIAL ORGANIC CHEMISTRY
EBK ESSENTIAL ORGANIC CHEMISTRY
3rd Edition
ISBN: 8220100659461
Author: Bruice
Publisher: PEARSON
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Chapter 16.8, Problem 14P
Interpretation Introduction

Interpretation:

An explanation for the use of trace amount of acid used in the formation of an N- glycoside has to be given.

Concept Introduction:

A N- glycoside is prepared by the reaction of a monosaccharide with an amine (base) in the presence of catalytic or traces amount of acid.

Amination reaction: Amination is the process by which an amine group is introduced into an organic molecule.

Glycoside formation: carbohydrates react with an alcohol in acid which produce both anomers acetals are formed, if alkoxy group points down then it is α, alkoxy group points up then it is β.

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Heparin is used as an anti-coagulant. A risk of heparin use is thrombocytopenia, or low platelet count. This risk is minimized with the use of low molecular weight heparins (LMWH), therefore it is desirable to separate LMWH from higher molecular weight heparins. The method of choice to do this is molecular exclusion chromatography. Below is a chromatogram from a molecular exclusion chromatographic run. Peaks ranging from A to J are clearly distinguishable. The heparin mixture that was analyzed had anywhere from 6 to 30 repeat units of monomer (where the heparin with 30 repeat units would be roughly five times the size of the heparin with six repeat units). a. Which letter most likely represents the peak with 6 repeat units given these heparin polymers were separated with molecular exclusion chromatography? b. Explain your reasoning describing the mechanism of retention in molecular exclusion chromatography. 100 80 60 60 Relative Abundance 40 40 E GH 20 20 B A 36 38 40 42 44 46 48 50 50…
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