A chito-oligosaccharide involved in root nodulation
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Product Categories

Product Type

Biochemicals
Carbohydrates
Natural Products

Research Area

Plant Biology

Penta-N-acetylchitopentaose

Item No. 16101

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-glucopyranosyl-(1→4)-O-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl-(1→4)-2-(acetylamino)-2-deoxy-D-glucose
CAS Number
36467-68-2
Synonyms
  • Chitinpentaose
  • N,N’,N’’,N’’’,N’’’’-Pentaacetylchitopentaose
Molecular Formula
C40H67N5O26
Formula Weight
1034.0
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
PBS (pH 7.2): 1 mg/ml
SMILES
O[C@@H]1[C@@H](CO)O[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@@]([C@H](O)CO)([H])[C@H](O)C(NC(C)=O)C=O)[C@H](NC(C)=O)[C@H]4O)O[C@@H]3CO)([H])[C@H](NC(C)=O)[C@H]2O)([H])[C@H](NC(C)=O)[C@H]1O
InChi Code
InChI=1S/C40H67N5O26/c1-12(52)41-17(6-46)27(58)33(18(57)7-47)68-38-24(43-14(3)54)30(61)35(20(9-49)65-38)70-40-26(45-16(5)56)32(63)36(22(11-51)67-40)71-39-25(44-15(4)55)31(62)34(21(10-50)66-39)69-37-23(42-13(2)53)29(60)28(59)19(8-48)64-37/h6,17-40,47-
InChi Key
DPTYILOGADPXRZ-NFYHBMEESA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $53

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    5 mg

    $169

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    10 mg

    $306

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    Product Description

    Root nodules, like those induced on the roots of leguminous plants by Rhizobium bacteria, are important sites for the conversion of atmospheric nitrogen into ammonia. The initiation and development of these growths are driven by a variety of nodulation (Nod) proteins produced by the infecting bacteria. Penta-N-acetylchitopentaose is a pentameric chito-oligosaccharide involved in nodulation. It can be produced by NodC, a chito-oligosaccharide synthase, and serve as a substrate for NodL, an O-acetyltransferase.1,2,3 This bacterial product binds plant root lectins, and this interaction may be important in the promotion of cell division in the root cortex.4,5 Penta-N-acetylchitopentaose, as well as chitin and chitosan, inhibits nitric oxide production in LPS-activated RAW 264.7 macrophages.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kamst, E., van der Drift, K.M., Thomas-Oates, J.E., et al. Mass spectrometric analysis of chitin oligosaccharides produced by Rhizobium NodC protein in Escherichia coli. J. Bacteriol. 177(21), 6282-6285 (1995).

    2. Huang, G.L., Zhang, D.W., Zhao, H.J., et al. Chemo-enzymatic synthesis of allyl penta-N-acetyl-chitopentaose. Bioorg. Med. Chem. Lett. 16(7), 2042-2043 (2006).

    3. Bloemberg, G.V., Thomas-Oates, J.E., Lugtenberg, B.J., et al. Nodulation protein NodL of Rhizobium leguminosarum O-acetylates lipo-oligosaccharides, chitin fragments and N-acetylglucosamine in vitro. Mol. Microbiol. 11(4), 793-804 (1994).

    4. Anantharam, V., Patanjali, S.R., Swamy, M.J., et al. Isolation, macromolecular properties, and combining site of a chito-oligosaccharide-specific lectin from the exudate of ridge gourd (Luffa acutangula). The Journal of Biological Chemisty 261(3), 14621-14627 (1986).

    5. Díaz, C.L., Spaink, H.P., and Kijne, J.W. Heterologous rhizobial lipochitin oligosaccharides and chitin oligomers induce cortical cell divisions in red clover roots, transformed with the pea lectin gene. Mol. Plant Microbe Interact. 13(3), 268-276 (2000).

    6. 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).