N-[(2R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide

• ChemBase ID: 133322
• Molecular Formular: C8H15NO6
• Molecular Mass: 221.2078
• Monoisotopic Mass: 221.08993721
• SMILES: CC(=O)NC1[C@@H](OC(C(C1O)O)CO)O
• Canonical SMILES: OCC1O[C@@H](O)C(C(C1O)O)NC(=O)C
• InChI: InChI=1S/C8H15NO6/c1-3(11)9-5-7(13)6(12)4(2-10)15-8(5)14/h4-8,10,12-14H,2H2,1H3,(H,9,11)/t4?,5?,6?,7?,8-/m1/s1
• InChIKey: OVRNDRQMDRJTHS-WTZNIHQSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• IUPAC Traditional name: N-[(2R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• Synonyms: Poly-(1→4)-β-N-acetyl-D-glucosamine; Chitin from shrimp shells; Chitin 来源于虾壳

Database IDs

• CAS Number: 1398-61-4
• EC Number: 215-744-3
• MDL Number: MFCD00466914
• PubChem SID: 162227599; 24893190; 24892942; 24893141
• PubChem CID: 6857375

CALCULATED PROPERTIES

• Acid pKa: 11.60413
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -3.2205749
• LogD (pH = 7.4): -3.2206008
• Log P: -3.2205744
• Molar Refractivity: 47.0247 cm^3
• Polarizability: 19.398714 Å^3
• Polar Surface Area: 119.25 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: coarse flakes; powder; purified powder

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Grade: practical grade
• Suitability: suitable as substrate for chitinase test; suitable for analysis of chitinase
• Ignition Residue: ~5%
• Mol. Weight: Mr ~400000(lit.)

DETAILS

Sigma Aldrich - C7170

Antigen Background
Chitin from shrimp shells is suitable for analysis of chitinase. It is a polysaccharide composed of N-acetyl-D-glucomasine that can also be used for the manufacture of glucosamine and chitosan.
Quality
Requires purification prior to use as a substrate for chitinase.
Application
Chitin, a β(1,4) polymer chain of N-acetyl-D glucosamine, is used as a substrate to identify, differentiate and characterize chitinase(s) and chitin deacetylase(s). Chitin may be used as a viscosity/thickening agent or binder.

Sigma Aldrich - C9752

Preparation Note
Purified by a modification of the method of Hirano, S. and Nagao, N., Agric. Biol. Chem., 52, 2111 (1988).
Application
Chitin, a β(1,4) polymer chain of N-acetyl-D glucosamine, is used as a substrate to identify, differentiate and characterize chitinase(s) and chitin deacetylase(s). Chitin may be used as a viscosity/thickening agent or binder.

Sigma Aldrich - C9213

Application
Chitin, a β(1,4) polymer chain of N-acetyl-D glucosamine, is used as a substrate to identify, differentiate and characterize chitinase(s) and chitin deacetylase(s). Chitin may be used as a viscosity/thickening agent or binder.

Sigma Aldrich - 22720

Other Notes
Can be chemically modified by deacetylation and further reactions on chitosan1; Useful as starting material for the enzymatic synthesis of oligosaccharides; potentially useful material for the removal of metals from contaminated water2

Sigma Aldrich - 22718

Other Notes
Review of properties and possible applications1; In immobilization techniques. Fructose production by immobilized inulinase2; In the bacterial production of N,N′-diacetylchitobiose3; Preparation of chitin gels4

Sigma Aldrich - 22719

Application
suitable as substrate for chitinase
Other Notes
For the immobilization of α-amylase1