124583-64-8Relevant academic research and scientific papers
Chemo-enzymatic synthesis of tetra-N-acetyl-chitotetraosyl allosamizoline
Huang, Gang-Liang,Mei, Xin-Ya,Zhang, Hou-Cheng,Wang, Peng-George
, p. 2860 - 2861 (2008/09/20)
A new compound 7, possessing a tetra-N-acetyl-chitotetraosyl moiety as a constituent, was synthesized by bacterial fermentation which used allosamizoline 6 as the initial acceptor.
Synthesis of the glucoallosamidin pseudo-disaccharide: Use of an efficient Hg(II) mediated cyclization
Shrader, William D.,Imperiali, Barbara
, p. 599 - 602 (2007/10/02)
The title compound 1a was prepared from cyclopentadienylthallium in 11 steps. The key component of the pseudo-disaccharide 1a, (-)-allosamizoline 2, was synthesized in 2 steps starting from the known cyclopentene 4 by formation of the aminoimidate 5 follo
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.
A general synthetic strategy toward aminocyclopentitol glycosidase inhibitors. Application of palladium catalysis to the synthesis of allosamizoline and mannostatin A
Trost, Barry M.,Van Vranken, David L.
, p. 444 - 458 (2007/10/02)
A general strategy for the synthesis of aminocyclopentitol glycosidase inhibitors has been applied to the synthesis of allosamizoline and mannostatin A. These cyclic pseudosugars are members of a growing family of highly potent and selective glycosidase i
