FComEx: Chitin (PC000734)

Record Information

Version

1.0

Creation date

2015-10-09 22:32:18 UTC

Update date

2017-01-19 02:36:34 UTC

FoodComEx ID

PC000734

FoodDB Record

FDB023154

Chemical Information

Name

Chitin

Description

Chitin is an unusual substance as it is a naturally occurring polymer. Its breakdown is conducted by bacteria which have receptors to simple sugars from the decomposition of chitin. If chitin is detected they then produce enzymes to digest the chitin by reducing it to simple sugars and ammonia. Chitin (IPA: [Kaitin]) is one of the main components in the cell walls of fungi, the exoskeletons of insects and other arthropods, and in some other animals. It is a polysaccharide; it is constructed from units of acetylglucosamine (more completely, N-acetyl-D-glucos-2-amine). These are linked together in beta-1,4 fashion (in a similar manner to the glucose units which form cellulose). In effect chitin may be described as cellulose with one hydroxyl group on each monomer replaced by an acetylamine group. This allows for increased hydrogen bonding between adjacent polymers, giving the polymer increased strength. A linear polysaccharide of beta-1->4 linked units of acetylglucosamine. It is the second most abundant biopolymer on earth, found especially in insects and fungi. When deacetylated it is called chitosan. [HMDB]

CAS Number

1398-61-4

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
[1,4-(N-Acetyl-beta-D-glucosaminyl)]n	hmdb
[1,4-(N-Acetyl-beta-D-glucosaminyl)]n+1	hmdb
[1,4-(N-Acetyl-beta-delta-glucosaminyl)]n	hmdb
[1,4-(N-Acetyl-beta-delta-glucosaminyl)]n+1	hmdb
beta-1,4-Poly-N-acetyl-D-glucosamine	hmdb
beta-1,4-Poly-N-acetyl-delta-glucosamine	hmdb
Poly 2-Acetamido-2-deoxy-D-glucose	hmdb
Poly 2-Acetamido-2-deoxy-delta-glucose	hmdb

Chemical Formula

C28H49N3O16

IUPAC name

N-[(2R,4S,5S)-5-({[(2R,4S,5S)-3-acetamido-5-({[(2R,4R,5S)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]methoxy}methyl)-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]methoxy}methyl)-2,4-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide

InChI Identifier

InChI=1S/C28H49N3O16/c1-11(35)29-21-19(9-44-8-15-17(5-33)47-28(42)23(25(15)39)31-13(3)37)45-16(4-32)14(24(21)38)7-43-10-20-22(30-12(2)36)27(41)26(40)18(6-34)46-20/h14-28,32-34,38-42H,4-10H2,1-3H3,(H,29,35)(H,30,36)(H,31,37)/t14-,15-,16?,17?,18?,19+,20+,21?,22?,23?,24+,25+,26-,27-,28-/m1/s1

InChI Key

DJHJJVWPFGHIPH-OODMECLYSA-N

Isomeric SMILES

CC(=O)NC1[C@H](O)OC(CO)[C@@H](COC[C@@H]2OC(CO)[C@@H](COC[C@@H]3OC(CO)[C@@H](O)[C@H](O)C3NC(C)=O)[C@H](O)C2NC(C)=O)[C@@H]1O

Average Molecular Weight

683.6992

Monoisotopic Molecular Weight

683.311282535

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as c-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a C-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

C-glycosyl compounds

Alternative Parents