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Topic: Chemistry name for N-linked saccharides?  (Read 3498 times)

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Offline NerdyGeek

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Chemistry name for N-linked saccharides?
« on: May 07, 2018, 10:33:58 PM »
I'm wondering what the chemistry term (not biochem) is for the highlighted N-linked saccharide bond below (link provided)? I've been looking through old chemistry books and cannot find any similar bonds.

https://imgur.com/V1JtXkx

Offline Borek

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Re: Chemistry name for N-linked saccharides?
« Reply #1 on: May 08, 2018, 02:45:46 AM »
So, basically you are asking what

[*:1]C(=O)N[*:2]

is?
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Offline sjb

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Re: Chemistry name for N-linked saccharides?
« Reply #2 on: May 08, 2018, 05:52:50 AM »
Sorry Borek, look again at the structure - it's more

[*]OC([*])([*])N([*])[*]

Offline Babcock_Hall

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Re: Chemistry name for N-linked saccharides?
« Reply #3 on: May 08, 2018, 10:14:38 AM »
@OP, Given that a forum rule is that you give your thoughts first, what name or names have you found so far?  DNA and RNA have a similar linkage.
« Last Edit: May 08, 2018, 10:48:01 AM by Babcock_Hall »

Offline Borek

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Re: Chemistry name for N-linked saccharides?
« Reply #4 on: May 08, 2018, 10:41:39 AM »
Sorry Borek, look again at the structure - it's more

[*]OC([*])([*])N([*])[*]

Perhaps you are right. What makes me wonder is that I doubt this particular arrangement of atoms can be treated separately when the nitrogen is a part of another, quite well know bond.
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Offline NerdyGeek

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Re: Chemistry name for N-linked saccharides?
« Reply #5 on: May 08, 2018, 10:53:15 AM »
@OP, Given that a forum rule is that you give your thoughts first, what name or names have you found so far?  DNA and RNA have a similar linkage.

I know its also called N-linked glycosylation in biochemistry, but the question specifically asks for it in chemistry terms. So would it just be a covalent bond? That's my struggle that I'm finding it in biochem terms not chem terms.

Offline Babcock_Hall

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Re: Chemistry name for N-linked saccharides?
« Reply #6 on: May 08, 2018, 11:01:41 AM »
Glycosides involving aldoses are a subclass of acetals.  The bond in question might be thought of as an N-acetal in which an amine replaces the alcohol of an acetal; however, I am not sure, given that the nitrogen of asparagine is in a functional group already.

Offline wildfyr

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Re: Chemistry name for N-linked saccharides?
« Reply #7 on: May 08, 2018, 11:41:24 AM »
I think we are looking for the term "hemiaminal ether" https://en.wikipedia.org/wiki/Aminal. However, since the nitrogen is part of an amide, it has quite different character than a "plain" aminal.

Anyways the glycosylamine wiki page https://en.wikipedia.org/wiki/Glycosylamine calls that linkage a hemiaminal ether or a  β-N-glycosidic bond.

Offline pgk

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Re: Chemistry name for N-linked saccharides?
« Reply #8 on: May 08, 2018, 01:53:25 PM »
It is an amide of hemiaminal ether that could be named “N-acyl-hemiaminal ether”, where acyl is the rest of the linkage or more simply: "glucosylamide".
« Last Edit: May 08, 2018, 03:29:29 PM by pgk »

Offline NerdyGeek

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Re: Chemistry name for N-linked saccharides?
« Reply #9 on: May 08, 2018, 04:51:00 PM »
I think we are looking for the term "hemiaminal ether" https://en.wikipedia.org/wiki/Aminal. However, since the nitrogen is part of an amide, it has quite different character than a "plain" aminal.

Anyways the glycosylamine wiki page https://en.wikipedia.org/wiki/Glycosylamine calls that linkage a hemiaminal ether or a  β-N-glycosidic bond.

Thank you! (Also thanks to everyone else)

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