N-acetylneuraminate
Description
N-Acetylneuraminic acid (Neu5Ac), also known as N-acetylneuraminate, is a derivative of neuraminic acid, which is a type of sialic acid. It is a negatively charged carbohydrate molecule that is commonly found on the surface of many animal cells and is involved in a variety of cellular processes.
In humans, Neu5Ac is involved in the synthesis of glycolipids and glycoproteins, which are important components of cell membranes. It also plays a role in the immune system, where it helps to regulate the activity of immune cells.
Neu5Ac is synthesized from UDP-glucose and N-acetylmannosamine by the enzyme UDP-N-acetylglucosamine 2-epimerase/N-acetylmannosamine kinase (GNE). Once synthesized, it is incorporated into glycoconjugates by a family of enzymes called sialyltransferases.
Deficiencies in the synthesis of Neu5Ac have been linked to a rare genetic disorder called hereditary inclusion body myopathy (HIBM), which is characterized by muscle weakness and wasting. In addition, Neu5Ac has been studied for its potential therapeutic applications, including as an anti-inflammatory agent and as a target for cancer therapy.
Chemical Formula:
C11H18NO9
Molecular Weight:
308.264 Daltons
Monoisotopic Mass:
308.264 Daltons
InChI:
1S/C11H19NO9/c1-4(14)12-7-5(15)2-11(20,10(18)19)21-9(7)8(17)6(16)3-13/h5-9,13,15-17,20H,2-3H2,1H3,(H,12,14)(H,18,19)/p-1/t5-,6+,7+,8+,9+,11?/m0/s1
InChIKey:
Synonyms
- sialic acid
- NANA
- O-sialic acid
- sialate
- N-acetylneuraminic acid
- Neu5Ac
- 5-acetamido-3,5-dideoxy-D-glycero-D-galacto-2-nonulosonic acid
- 5-acetamido-3,5-dideoxy-D-glycero-D-galacto-non-2-ulopyranosonic acid
Databases
BiGG:
acnam
ChEBI:
35418
PubChem (CID):
6857396
KEGG:
C00270
MetaCyc:
N-ACETYLNEURAMINATE
CAS:
131-48-6