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Topic: 1,4-glycosidic bond  (Read 4867 times)

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Offline jsmith613

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1,4-glycosidic bond
« on: September 27, 2010, 03:33:06 PM »
Why is the 1,4-glycosidic bond called so. (combination of two alpha-glucose molecules)
I am most intersetd in the 'ic' part - when we have carboxyllic acids i would expect 'ic'. Why is it there

Offline Dan

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Re: 1,4-glycosidic bond
« Reply #1 on: September 28, 2010, 05:29:55 AM »
Glycoside is is a defined term, essentially a sugar fragment (a glycosyl group) with something bonded to the anomeric  position (the 1 position for aldoses) through an O - in the case you describe, that "something" is another molecule of glucose, and the O through which it is bonded is at position 4, hence 1,4.

This bond to the anomeric positon is called a glycosidic bond to distingush it from all the other bonds, specifying the the bond in question links the glycosyl group with the "something else". The suffix "ic" is not suggestive of a carboxylic acid - the term carboxylic acid basically means: an acid associated with a carboxyl group. Similarly a glycosidic bond is: a bond associated with a glycosyl group.

This kind of terminology is common, you might say to your labmates, "Hmm, that signal in your NMR spectrum looks like an aldehydic proton" - meaning it looks like the proton associated with the aldehyde group - or "the allylic alcohol can be selectively oxidised" or "Shall we go and get an alcoholic drink after we've finished these columns?"...
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