243975-37-3Relevant academic research and scientific papers
Solution-phase total synthesis of the hydrophilic natural product argifin using 3,4,5-tris(octadecyloxy)benzyl tag
Hirose, Tomoyasu,Kasai, Takako,Akimoto, Takafumi,Endo, Ayako,Sugawara, Akihiro,Nagasawa, Kazuo,Shiomi, Kazuro,Omura, Satoshi,Sunazuka, Toshiaki
experimental part, p. 6633 - 6643 (2011/09/30)
A solution-phase total synthesis of argifin using 3,4,5-tris(octadecyloxy) benzyl tag as a hydrophobic protective group of carboxylic acid was developed to produce 44% overall yield for 16 linear steps. Argifin, a novel class of natural product chitinase
Solid-phase synthesis of cyclic peptide chitinase inhibitors: SAR of the argifin scaffold
Dixon, Mark J.,Nathubhai, Amit,Andersen, Ole A.,Van Aalten, Daan M. F.,Eggleston, Ian M.
experimental part, p. 259 - 268 (2009/03/11)
A new, highly efficient, all-solid-phase synthesis of argifin, a natural product cyclic pentapeptide chitinase inhibitor, is reported. The synthesis features attachment of an orthogonally protected Asp residue to the solid support and assembly of the line
Argifin; efficient solid phase total synthesis and evalution of analogues of acyclic peptide
Sunazuka, Toshiaki,Sugawara, Akihiro,Iguchi, Kanami,Hirose, Tomoyasu,Nagai, Kenichiro,Noguchi, Yoshihiko,Saito, Yoshifumi,Yamamoto, Tsuyoshi,Ui, Hideaki,Gouda, Hiroaki,Shiomi, Kazuro,Watanabe, Takeshi,Omura, Satoshi
experimental part, p. 2751 - 2758 (2009/08/15)
An effective solid phase synthesis of Argifin, providing subsequent access to effective synthesis of analogues, was developed in 13% overall yield, as well as elucidating structure-activity relationships. The novel acyclic peptide 18b, prepared from a synthetic intermediate of Argifin, was found to be 70 times more potent as an inhibitor of Serratia marcescens chitinases B than Argifin itself.
An efficient synthesis of argifin: A natural product chitinase inhibitor with chemotherapeutic potential
Dixon, Mark J.,Andersen, Ole A.,Van Aalten, Daan M. F.,Eggleston, Ian M.
, p. 4717 - 4721 (2007/10/03)
The first synthesis of the cyclopentapeptide family 18 chitinase inhibitor argifin has been achieved by a combination of solid phase and solution chemistry. Synthetic argifin is a nanomolar inhibitor of chitinase B1 from Aspergillus fumigatus and the high-resolution X-ray structure of the synthesized material in complex with the same enzyme is identical to that previously obtained for the natural product.
