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Review
. 2019 Dec;34(1):1226-1232.
doi: 10.1080/14756366.2019.1623208.

Synthesis, antiasthmatic, and insecticidal/antifungal activities of allosamidins

Gangliang Huang  1 , Hualiang Huang  2
Affiliations
Review

Synthesis, antiasthmatic, and insecticidal/antifungal activities of allosamidins

Gangliang Huang et al. J Enzyme Inhib Med Chem. 2019 Dec.

Abstract

Allosamidins come from the secondary metabolites of Streptomyces species, and they have the pseudotrisaccharide structures. Allosamidins are chitinase inhibitors that can be used to study the physiological effects of chitinases in a variety of organisms. They have the novel antiasthmatic activity and insecticidal/antifungal activities. Herein, the synthesis and activities of allosamidins were summarized and analyzed.

Keywords: Allosamidins; antiasthmatic activity; insecticidal/antifungal activities; synthesis.

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Figures

Figure 1.
Figure 1.
Structures of allosamidin 1 and allosamizoline 2.
Scheme 1.
Scheme 1.
Preparation of (-)-allosamizoline 2.
Scheme 2.
Scheme 2.
Preparation of mannosamine derivatives with oxazolidinone protection.
Scheme 3.
Scheme 3.
Synthesis of donor 8 with N-Cbz protection.
Scheme 4.
Scheme 4.
Synthesis of donor 9 with N-Cbz protection.
Scheme 5.
Scheme 5.
Solid phase synthesis of allosamidin 1.
Scheme 6.
Scheme 6.
Synthesis of chitobiose and chitotriose thiazolines (24 and 25), and their thioamide analogues (30 and 31).
Scheme 7.
Scheme 7.
Solid phase synthesis of chitotriose thiazoline 25.
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References

    1. Sakuda S, Isogai A, Matsumoto S, Suzuki A. Search for microbial insect growth regulators. II. Allosamidin, a novel insect chitinase inhibitor. J Antibiot 1987;40:296–300. - PubMed
    1. Sakuda S, Isogai A, Matsumoto S, et al. . The structure of allosamidin, a novel insect chitinase inhibitor, produced by Streptomyces Sp. Tetrahedron Lett 1986;27:2475–8.
    1. Takahashi S, Terayama H, Koshino H, Kuzuhara H. Synthesis of a novel azapseudodisaccharide related to allosamidin employing N,N'-diacetylchitobiose as a key starting material. Tetrahedron 1999;55:14871–84.
    1. Blattner R, Gerard PJ, Spindler-Barth M. Synthesis and biological activity of allosamidin and allosamidin analogues. Pestic Sci 1997;50:312–8.
    1. Blattner R, Furneaux RH, Lynch GP. Synthesis of allosamidin analogues. Carbohydr Res 1996;294:29–39. - PubMed

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