Solution-phase total synthesis of the hydrophilic natural product argifin using 3,4,5-tris(octadecyloxy)benzyl tag
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
Argifin; efficient solid phase total synthesis and evalution of analogues of acyclic peptide
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.
Solid-phase synthesis of cyclic peptide chitinase inhibitors: SAR of the argifin scaffold
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
Dixon, Mark J.,Nathubhai, Amit,Andersen, Ole A.,Van Aalten, Daan M. F.,Eggleston, Ian M.
experimental part
p. 259 - 268
(2009/03/11)
An efficient synthesis of argifin: A natural product chitinase inhibitor with chemotherapeutic potential
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.
Dixon, Mark J.,Andersen, Ole A.,Van Aalten, Daan M. F.,Eggleston, Ian M.
p. 4717 - 4721
(2007/10/03)
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