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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: NerdyGeek on May 07, 2018, 10:33:58 PM

Title: Chemistry name for N-linked saccharides?
Post by: NerdyGeek 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
Title: Re: Chemistry name for N-linked saccharides?
Post by: Borek on May 08, 2018, 02:45:46 AM
So, basically you are asking what

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

is?
Title: Re: Chemistry name for N-linked saccharides?
Post by: sjb on May 08, 2018, 05:52:50 AM
Sorry Borek, look again at the structure - it's more

[*]OC([*])([*])N([*])[*]
Title: Re: Chemistry name for N-linked saccharides?
Post by: Babcock_Hall 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.
Title: Re: Chemistry name for N-linked saccharides?
Post by: Borek on May 08, 2018, 10:41:39 AM
Quote from: sjb on May 08, 2018, 05:52:50 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.
Title: Re: Chemistry name for N-linked saccharides?
Post by: NerdyGeek on May 08, 2018, 10:53:15 AM
Quote from: Babcock_Hall 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.

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.
Title: Re: Chemistry name for N-linked saccharides?
Post by: Babcock_Hall 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.
Title: Re: Chemistry name for N-linked saccharides?
Post by: wildfyr 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.
Title: Re: Chemistry name for N-linked saccharides?
Post by: pgk 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".
Title: Re: Chemistry name for N-linked saccharides?
Post by: NerdyGeek on May 08, 2018, 04:51:00 PM
Quote from: wildfyr 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.

Thank you! (Also thanks to everyone else)