A hexamer of N-acetylglucosamine
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Hexa-N-acetylchitohexaose

Item No. 17864

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
O-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl-(1→4-O-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl-(1→4)-O-2-(acetylamino)-2-deoxy-β-D-glucopyranosy-(1→4)-O-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl-(1→4)-O-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl-(1→4)-2-(acetylamino)-2-deoxy-D-glucose
CAS Number
38854-46-5
Synonyms
  • N-Acetylchitohexaose
  • NACOS-6
Molecular Formula
C48H80N6O31
Formula Weight
1237.2
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
PBS (pH 7.2): 10 mg/ml
SMILES
OC[C@H]1O[C@](O[C@@H]2[C@@H](CO)O[C@](O[C@H]3[C@H](O)[C@@H](NC(C)=O)[C@H](O[C@]4([H])[C@@H](CO)O[C@@H](O[C@@]5([H])[C@H](O)[C@@H](NC(C)=O)[C@H](O[C@@]([C@H](O)CO)([H])[C@H](O)[C@@H](NC(C)=O)C=O)O[C@@H]5CO)[C@H](NC(C)=O)[C@H]4O)O[C@@H]3CO)([H])[C@H](N
InChi Code
InChI=1S/C48H80N6O31/c1-14(62)49-20(7-55)32(69)39(21(68)8-56)81-45-28(51-16(3)64)35(72)41(23(10-58)77-45)83-47-30(53-18(5)66)37(74)43(25(12-60)79-47)85-48-31(54-19(6)67)38(75)42(26(13-61)80-48)84-46-29(52-17(4)65)36(73)40(24(11-59)78-46)82-44-27(50-1
InChi Key
FUHDMRPNDKDRFE-LPUYKFNUSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Hexa-N-acetylchitohexaose is a hexamer of N-acetylglucosamine, a subunit of the natural polymer chitin. It functions as an elicitor in plants, inducing the expression of chitinases.1,2 Like chitin and some of its derivatives, hexa-N-acetylchitohexaose is a substrate of lysozyme.3 It also binds LysM domains on certain proteins, including an endopeptidase of T. thermophilus.4 Hexa-N-acetylchitohexaose heightens the immune response against Pseudomonas and Listeria in mice, stimulates cytokine secretion in mesenchymal stem cells, and inhibits nitric oxide production by activated macrophages.5,6,7,8

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Inui, H., Yamaguchi, Y., and Hirano, S. Elicitor actions of N-acetylchitooligosaccharides and laminarioligosaccharides for chitinase and L-phenylalanine ammonia-lyase induction in rice suspension culture. Biosci. Biotechnol. Biochem. 61(6), 975-978 (1997).

    2. Gao, Y., Zan, X.L., Wu, X.F., et al. Identification of fungus-responsive cis-acting element in the promoter of Brassica juncea chitinase gene, BjCHI1. Plant Sci. 215-216, 190-198 (2014).

    3. Ouyang, Z., Takáts, Z., Blake, T.A., et al. Preparing protein microarrays by soft-landing of mass-selected ions. Science 301(5638), 1351-1354 (2003).

    4. Wong, J.E.M.M., Midtgaard, S.R., Gysel, K., et al. An intermolecular binding mechanism involving multiple LysM domains mediates carbohydrate recognition by an endopeptidase. Acta Crystallogr. D Biol. Crystallogr. 71(Pt 3), 592-605 (2014).

    5. Tokoro, A., Kobayashi, M., Tatewaki, N., et al. Protective effect of N-acetyl chitohexaose on Listeria monocytogenes infection in mice. Microbiol. Immunol. 33(4), 357-367 (1989).

    6. Okawa, Y., Kobayashi, M., Suzuki, S., et al. Comparative study of protetive effects of chitin, chitosan, and N-acetyl chitohexaose against Pseudomonas aeruginosa and Listeria monocytogenes infections in mice. Biol. Pharm. Bull. 26(6), 902-904 (2003).

    7. Lieder, R., Thormodsson, F., Ng, C.H., et al. Chitosan and chitin hexamers affect expansion and differentiation of mesenchymal stem cells differently. Int. J. Biol. Macromol. 51(4), 675-680 (2012).

    8. Hwang, S.M., Chen, C.Y., Chen, S.S., et al. Chitinous materials inhibit nitric oxide production by activated RAW 264.7 macrophages. Biochem. Biophys. Res. Commun. 271(1), 229-233 (2000).