126399-05-1Relevant articles and documents
Facile and rapid access to linear and truncated microcystin analogues for the implementation of immunoassays
Clave,Ronco,Boutal,Kreich,Volland,Franck,Romieu,Renard
experimental part, p. 676 - 690 (2010/05/02)
A series of simplified microcystin-LR analogues based on Adda [(2S,3S,8S,9S,4E,6E)-3-amino-9-methoxy-2,6,8-trimethyl-10-phenyldecadienoic acid] or its corresponding aldol precursor linked to a polypeptide moiety have been synthesised and assessed for thei
Total synthesis of motuporin and 5-[L-Ala]-motuporin
Samy, Raghu,Kim, Hong Yong,Brady, Matthew,Toogood, Peter L.
, p. 2711 - 2728 (2007/10/03)
Total synthesis of the cyclic peptide hepatotoxin motuporin is described, including an efficient synthesis of the constituent amino acid Adda. Three strategies to motuporin are outlined with their relative strengths and weaknesses. Cyclization of the linear peptide precursor was found to proceed moderately well for peptides containing the N- methyldehydrobutyrine residue masked as a threonine, but significant C- terminal epimerization occurred in the presence of the dehydroamino acid. Replacement of the N-methyldehydrobutyrine residue by L-alanine was explored to assess the contribution of this dehydroamino acid to the biochemical activity of motuporin. Some epimerization also was observed during cyclization of the alanine-containing peptide. Synthetic motuporin and both isomers of 5-[L-Ala]-motuporin inhibit the activity of protein phosphatase-1 (PP1) in rat adipocyte lysates with comparable IC50 values. These results indicate that the N-methyldehydrobutyrine residue is not essential for PP1 inhibition.
Total synthesis of motuporin (nodularin-v)
Bauer, Shawn M.,Armstrong, Robert W.
, p. 6355 - 6366 (2007/10/03)
The serine/threonine phosphatase (protein phosphatase 1 and 2A) inhibitors constitute a biologically and structurally interesting class of natural products. Among this class of inhibitors are cyclic pentapeptides (nodularins) and cyclic heptapeptides (mic
