176666-84-5Relevant articles and documents
Concise Synthesis of All Stereoisomers of Dendroamide A by Fluorous Mixture Synthesis Based on Fluorous-Fmoc Protection of Amino Acids
Takahashi, Hiroaki,Endo, Natsuki,Takanose, Hitomi,Sugiyama, Yuya,Eguchi, Fumitaka,Oguri, Kazuma,Hamamoto, Hiromi,Shioiri, Takayuki,Matsugi, Masato
, p. 3971 - 3982 (2015)
A liquid-phase split-type synthesis of all the stereoisomers of dendroamide A, which exhibits multidrug-resistance reversing activity, has been carried out. The key to the concise synthesis was the fluorous-Fmoc protection strategy of each of the starting
Total synthesis of dendroamide A, a novel cyclic peptide that reverses multiple drug resistance
Xia,Smith
, p. 3459 - 3466 (2001)
Dendroamide A (1) was isolated from a blue-green alga on the basis of its ability to reverse drug resistance in tumor cells that overexpress either of the transport proteins, P-glycoprotein or MRP1. Because of this activity, methods for the synthesis of analogues of this oxazole- and thiazole-containing cyclic peptide have been developed; and the total synthesis of 1 has been completed. Highlights of the synthetic strategy are as follows: (1) a dicyclohexylcarbodiimide coupling of D-Ala and L-Thr, followed by reaction with Burgess reagent and DBU-assisted oxidation to form D-Alaoxazole; (2) formation of D-Val-thiazole and D-Ala-thiazole via modified Hantzsch reactions; and (3) use of molecular modeling to select the preferred precursor for the final cyclization of the peptide analogue. Synthetic 1 demonstrated spectral properties identical to those of the natural product and reversed P-glycoprotein-mediated drug resistance more effectively than MRP1-mediated resistance. Certain of the synthetic precursors had biological activity, indicating that cell permeability and peptide cyclization are necessary for optimal activity. Thus, the structure and the biological activities of the natural product are confirmed, and methods for the synthesis of analogues for further structure-activity explorations are defined.
New total synthesis of dendroamide a from dehydrodi- and tripeptides
Yonezawa, Yasuchika,Tani, Naoki,Shin, Chung-gi
, p. 95 - 105 (2007/10/03)
New total synthesis of triheterocyclic cyclopeptide bistratamide-type dendroamide A, isolated from the cyanobacterium Stigonema dendroideum, was achieved by various conversions of Δ1-dehydrodi- and Δ3-dehydrotripeptides.
