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N-Acetylglucosamine

 
N Acetylglucosamine

 
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N-Acetylglucosamine
 
 
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N-Acetylglucosamine (N-Acetyl-D-Glucosamine, or GlcNAc, or NAG) is a monosaccharide
Monosaccharide

Monosaccharides are the most basic unit of carbohydrates. They are the simplest form of sugar and are usually colorless, water-soluble, crystal solids....
 derivative of glucose
Glucose

Glucose , a monosaccharide also known as grape sugar, blood sugar, or corn sugar, is a very important carbohydrate in biology....
. Chemically it is an amide between glucosamine
Glucosamine

Glucosamine is an amino sugar and a prominent precursor in the biochemical synthesis of glycosylation proteins and lipids. A type of glucosamine forms chitosan and chitin, which composes the exoskeletons of crustaceans and other arthropods, cell walls in fungi and many higher organisms....
 and acetic acid
Acetic acid

Acetic acid, CH3COOH, also known as ethanoic acid, is an organic acid which gives vinegar its sour taste and pungent smell. Pure, water-free acetic acid is a colourless liquid that absorbs water from the environment , and freezes at 16.7 Celsius to a colourless crystalline solid....
. It has a molecular formula of C
Carbon

Carbon is a chemical element with chemical symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalence?making four electrons available to form covalent bond chemical bonds....
8H
Hydrogen

Hydrogen is the chemical element with atomic number 1. It is represented by the chemical symbol H. At standard temperature and pressure, hydrogen is a colorless, odorless, nonmetallic, tasteless, highly combustion and explosive Diatomic molecule gas with the molecular formula H2....
15N
Nitrogen

Nitrogen is a chemical element that has the symbol N and atomic number 7 and atomic mass 14.00674?. Elemental nitrogen is a colorless, odorless, tasteless and mostly inert diatomic gas at standard conditions, constituting 78% by volume of Earth's atmosphere....
O
Oxygen

Oxygen no O2 produced; 2) O2 produced, but absorbed in oceans & seabed rock; 3) O2 starts to gas out of the oceans, but is absorbed by land surfaces and formation of ozone layer; 4-5) O2 sinks filled and the gas accumulates]]...
6, a molar mass
Molar mass

Molar mass, symbol M, is the mass of one mole of a substance . It is a physical property which is characteristic of each pure substance. The base SI unit for mass is the kilogram but, for both practical and historical reasons, molar masses are almost always quoted in grams per mole , especially in chemistry....
 of 221.21 g/mol, and it is significant in several biological systems.

It is part of a biopolymer in the bacterial cell wall
Cell wall

A cell wall is a tough, flexible and sometimes fairly rigid layer that surrounds some types of cell . It is located outside the cell membrane and provides these cells with structural support and protection, and also acts as a filtering mechanism....
, built from alternating units of GlcNAc and N-acetylmuramic acid
N-Acetylmuramic acid

N-Acetylmuramic acid, or MurNAc, is the ether of lactic acid and N-acetylglucosamine with a chemical formula of Carbon11Hydrogen19NitrogenOxygen8....
 (MurNAc), cross-linked with oligopeptides at the lactic acid
Lactic acid

Lactic acid , also known as milk acid, is a chemical compound that plays a role in several biochemistry processes. It was first isolated in 1780 by a Swedish chemist, Carl Wilhelm Scheele, and is a carboxylic acid with a chemical formula of C3H6O3....
 residue of MurNAc.






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N-Acetylglucosamine (N-Acetyl-D-Glucosamine, or GlcNAc, or NAG) is a monosaccharide
Monosaccharide

Monosaccharides are the most basic unit of carbohydrates. They are the simplest form of sugar and are usually colorless, water-soluble, crystal solids....
 derivative of glucose
Glucose

Glucose , a monosaccharide also known as grape sugar, blood sugar, or corn sugar, is a very important carbohydrate in biology....
. Chemically it is an amide between glucosamine
Glucosamine

Glucosamine is an amino sugar and a prominent precursor in the biochemical synthesis of glycosylation proteins and lipids. A type of glucosamine forms chitosan and chitin, which composes the exoskeletons of crustaceans and other arthropods, cell walls in fungi and many higher organisms....
 and acetic acid
Acetic acid

Acetic acid, CH3COOH, also known as ethanoic acid, is an organic acid which gives vinegar its sour taste and pungent smell. Pure, water-free acetic acid is a colourless liquid that absorbs water from the environment , and freezes at 16.7 Celsius to a colourless crystalline solid....
. It has a molecular formula of C
Carbon

Carbon is a chemical element with chemical symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalence?making four electrons available to form covalent bond chemical bonds....
8H
Hydrogen

Hydrogen is the chemical element with atomic number 1. It is represented by the chemical symbol H. At standard temperature and pressure, hydrogen is a colorless, odorless, nonmetallic, tasteless, highly combustion and explosive Diatomic molecule gas with the molecular formula H2....
15N
Nitrogen

Nitrogen is a chemical element that has the symbol N and atomic number 7 and atomic mass 14.00674?. Elemental nitrogen is a colorless, odorless, tasteless and mostly inert diatomic gas at standard conditions, constituting 78% by volume of Earth's atmosphere....
O
Oxygen

Oxygen no O2 produced; 2) O2 produced, but absorbed in oceans & seabed rock; 3) O2 starts to gas out of the oceans, but is absorbed by land surfaces and formation of ozone layer; 4-5) O2 sinks filled and the gas accumulates]]...
6, a molar mass
Molar mass

Molar mass, symbol M, is the mass of one mole of a substance . It is a physical property which is characteristic of each pure substance. The base SI unit for mass is the kilogram but, for both practical and historical reasons, molar masses are almost always quoted in grams per mole , especially in chemistry....
 of 221.21 g/mol, and it is significant in several biological systems.

It is part of a biopolymer in the bacterial cell wall
Cell wall

A cell wall is a tough, flexible and sometimes fairly rigid layer that surrounds some types of cell . It is located outside the cell membrane and provides these cells with structural support and protection, and also acts as a filtering mechanism....
, built from alternating units of GlcNAc and N-acetylmuramic acid
N-Acetylmuramic acid

N-Acetylmuramic acid, or MurNAc, is the ether of lactic acid and N-acetylglucosamine with a chemical formula of Carbon11Hydrogen19NitrogenOxygen8....
 (MurNAc), cross-linked with oligopeptides at the lactic acid
Lactic acid

Lactic acid , also known as milk acid, is a chemical compound that plays a role in several biochemistry processes. It was first isolated in 1780 by a Swedish chemist, Carl Wilhelm Scheele, and is a carboxylic acid with a chemical formula of C3H6O3....
 residue of MurNAc. This layered structure is called peptidoglycan
Peptidoglycan

Peptidoglycan, also known as murein, is a polymer consisting of sugars and amino acids that forms a mesh-like layer outside the plasma membrane of bacteria, forming the cell wall....
.

GlcNAc is the monomeric unit of the polymer chitin
Chitin

Chitin n is a long-chain polymer of a N-acetylglucosamine, a derivative of glucose, and is found in many places throughout the natural world....
, which forms the outer coverings of insect
Insect

Insects are the biggest class of arthropods and the only ones with wings. They are the most diverse group of animals on the planet. They are most diverse at the equator and their diversity declines toward the poles....
s and crustacean
Crustacean

Crustaceans are a large group of arthropods, comprising almost 52,000 described species , and are usually treated as a subphylum . They include various familiar animals, such as crabs, lobsters, crayfish, shrimp, krill and barnacles....
s. GlcNAc is also of note in neurotransmission
Neurotransmission

Neurotransmission , also called synaptic transmission, is an electrical movement within synapses caused by a propagation of nerve impulses....
, where it is thought to be an atypical neurotransmitter
Neurotransmitter

Neurotransmitters are chemistry which relay, amplify and modulate signals between a neuron and another cell . Neurotransmitters are packaged into vesicles that cluster beneath the membrane on the presynaptic side of a synapse, and are released into the synaptic cleft, where they bind to receptors in the membrane on the postsynaptic side of...
 functioning in nocioceptive (pain
Pain

Pain, in the sense of physical pain, is a typical sensory experience that may be described as the unpleasant awareness of a noxious stimulus or bodily harm....
) pathways.

Polymerized with glucuronic acid
Glucuronic acid

Glucuronic acid is a carboxylic acid. Its structure is similar to that of glucose. However, glucuronic acid's sixth carbon is oxidized to a carboxylic acid....
 it forms hyaluronan
Hyaluronan

Hyaluronan is a non-sulfated glycosaminoglycan distributed widely throughout connective tissue, epithelial tissue, and neural tissues. It is one of the chief components of the extracellular matrix, contributes significantly to cell proliferation and migration, and may also be involved in the progression of some malignant tumors....
.

Medical uses

It has been proposed as a treatment for autoimmune diseases.

See also

  • Keratan sulfate
    Keratan sulfate

    Keratan sulfate , also called keratosulfate, is any of several Sulfuric_acid glycosaminoglycans that have been found especially in the cornea, cartilage, and bone....
  • Chitin
    Chitin

    Chitin n is a long-chain polymer of a N-acetylglucosamine, a derivative of glucose, and is found in many places throughout the natural world....
  • N-acetyllactosamine synthase
    N-acetyllactosamine synthase

    N-acetyllactosamine synthase is a galactosyltransferase enzyme.It is a component of lactose synthase.It is classified under .See also...


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