103782-08-7Relevant articles and documents
Syntheses and activity of carbohydrate-containing chitinase inhibitors
Huang, Gangliang,Mei, Xinya,Chen, Xin,Wang, Xiaomei
, p. 828 - 832 (2015/11/18)
The pseudo-Trisaccharide allosamidin 1 is a potent inhibitor of all family 18 chitinases, and it is confirmed to have insecticidal and antifungal activities. However, the synthesis of allosamidins is very difficult, and it is a challengeable subject. Allosamidins were synthesized in solid/liquid phase and total solid phase, respectively. Solid/liquid-phase method realizes the partial solid-phase synthesis of allosamidins. Total solid-phase method greatly simplifies the purification process. Moreover, it indicated that the inhibitory activity of N,N'-diacetyl-β-chitobiosylallosamizoline 9 against chitinase from Bombyx mori was a little weaker than that of allosamidin 1.
An efficient synthesis of allosamidin
Huang, Gangliang,Shu, Shuangquan
scheme or table, p. 1829 - 1831 (2012/08/29)
The solid-phase synthesis of allosamidin was investigated. After two N-benzyloxycarbonyl (Cbz)-protected trichloroacetimidate donors were synthesized, the solid-phase synthesis was performed using polystyrene as support and an o-nitrobenzyl ether tether as linker. The target allosamidin was efficiently obtained by iterative glycosylation reactions, catalytic hydrogenation, acetylation, deacetylation, and photolysis.
Solid-phase synthesis of allosamidin
Huang, Gang Liang,Dai, Yue Peng
scheme or table, p. 1554 - 1556 (2010/08/22)
The solid-phase synthesis of allosamidin is described. After the NHCbz trichloroacetimidate donors were synthesized, solid-phase synthesis was performed using the Wang resin as support. The target allosamidin was obtained by iterative glycosylation reactions, catalytic hydrogenation, acetylation, and deacetylation, respectively. Georg Thieme Verlag Stuttgart New York.
The total synthesis of allosamidin. Expansions of the methodology of azaglycosylation pursuant to the total synthesis of allosamidin. A surprising enantiotopic sense for a lipase-induced deacetylation
Griffith, David A.,Danishefsky, Samuel J.
, p. 9526 - 9538 (2007/10/03)
Allosamidin, recently isolated from mycelial extracts of Streptomyces sp. 1713, is a powerful and selective chitinase inhibitor. The total synthesis of allosamidin is described herein. The electric eel acetylcholinesterase-mediated enantioselective hydrolysis of (trans,trans)-2-(benzyloxy)cyclopentene-1,3-diol diacetate accessed a monoacetyl derivative. Five additional steps produced a protected version of the aglycon ('allosamizoline') sector of allosamidin. An allal derivative stereoselectively reacted with benzenesulfonamide in the presence of a halonium source to afford a 2β-halo-1α-sulfonamidohexose. Treatment of this product with a strong base generated an intermediate 1,2-sulfonylaziridine, which was trapped with a protected allal derivative to provide a disaccharide glycal. Reiteration of this scheme gave access to the required trisaccharide. Following deprotection, the total synthesis of allosamidin was accomplished. In addition, the method, with modification, gave access to several allosamidin analogs.
Syntheses of the Fungicide/Insecticide Allosamidin and a Structural Isomer
Blattner, Regine,Furneaux, Richard H.,Kemmitt, timothy,Tyler, Peter C.,Ferrier, Robert J.,Tiden, Anna-Karin
, p. 3411 - 3422 (2007/10/02)
A synthesis of the naturally occurring inhibitor of chitin metabolism, allosamidin 1, involves, as the key step, condensation between the allosamizoline derivative 39, prepared following oxyamination of the cyclopentene 19, and the disaccharide glycosylating agent 54 which was synthesised from 2-acetamido-2-deoxy-D-glucose.The structural isomer 59 of allosamidin is also reported.Brief biological test results obtained using isomers 1 and 59 are recorded.
Total synthesis of (-)-allosamidin, an insect chitinase inhibitor, employing chitin as a key starting material
Takahashi,Terayama,Kuzuhara
, p. 7565 - 7568 (2007/10/02)
(-)-Allosamidin (1), a novel insect chitinase inhibitor, was stereoselectively synthesized from di- and monosaccharidic constituents of chitin, N,N'-diacetylchitobiose (2) and D-glucosamine (3).
Synthesis of Allosamidin
Maloisel, Jean-Luc,Vasella, Andrea,Trost, Barry M.,Vranken, David L. van
, p. 1515 - 1526 (2007/10/02)
The previously prepared disaccharide 2 was deprotected (-> 3) and transformed into the trichloroacetimidate 4.In the presence of Me3SiOTf, 4 reacted regioselectively with the racemic allosamizoline benzyl ether 5, to yield (61 percent) the pseudotrisaccharides 7-10 (44:40:9:7) and the elimination product 6 (Scheme 1).Selective dephthaloylation (MeNH2, MeOH) of 7 and 8, followed by acetylation, gave 12 (73 percent) and 13 (74 percent), respectively (Scheme 2); harsher conditions (NH2NH2*H2O, EtOH, reflux), followed by acetylation, transformed 7 into 11.Deacetylation of 11-13 yielded 14-16, respectively.Allosamidin (1) was obtained in high yield by hydrogenation of 15 under acidic conditions (Scheme 3).Similarly, 16 and 14 were transformed into 17 and 18, respectively.Preliminary data on the inhibition of endochitinases by 1 and 17 are reported.
Biosynthetic Studies on the Chitinase Inhibitor, Allosamidin. Origin of the Carbon and Nitrogen Atoms.
Zhou, Ze-Yang,Sakuda, Shohei,Yamada, Yasuhiro
, p. 1649 - 1652 (2007/10/02)
Allosamidin 1 is a potent insect chitinase inhibitor produced by Streptomyces sp.The biosynthesis of compound 1 was studied by feeding experiments with labelled precursors.Incorporation experiments using - and D-glucose as well as doubly labelled D-glucosamine revealed that each skeleton of N-acetyl-D-allosamine and allosamizoline 2 was derived grom D-glucosamine.Further experiments with L-arginine and -methionine clarified the origin of the dimethylaminooxazoline moiety of compound 2.
Synthesis of Allosamidin
Maloisel, Jean-Luc,Vasella, Andrea,Trost, Barry M.,Vranken, David L. van
, p. 1099 - 1100 (2007/10/02)
Allosamidin, a novel chitinase inhibitor has been synthesized by a convergent approach using a regioselective glycosidation of a racemic allosamizoline derivative, with a disaccharide trichloroacetamidate.
