[NerdyGeek]

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

[Borek]

So, basically you are asking what



is?

[sjb]

Sorry Borek, look again at the structure - it's more

[Babcock_Hall]

@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.

[Borek]

Sorry Borek, look again at the structure - it's more

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.

[NerdyGeek]

@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.

[Babcock_Hall]

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.

[wildfyr]

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.

[pgk]

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".

[NerdyGeek]

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)