73584-84-6Relevant academic research and scientific papers
Highly Convergent Total Synthesis and Assignment of Absolute Configuration of Majusculamide D, a Potent and Selective Cytotoxic Metabolite from Moorea sp.
Caro-Diaz, Eduardo J. E.,Valeriote, Frederick A.,Gerwick, William H.
supporting information, p. 793 - 796 (2019/02/07)
The total synthesis of majusculamide D (MJS-D) is described, a lipopentapeptide originally isolated from Lyngbya majuscula and reisolated from a Moorea sp. MJS-D possesses selective and potent cancer cell toxicity. A scalable and convergent strategy with a minimal number of purifications produced significant quantities of MJM-D for in vivo evaluations. The absolute configuration of the 1,3-dimethyl-octanamide motif was determined by synthesis of this fragment via ZACA chemistry.
Renin Inhibitors
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Page/Page column 58, (2010/12/29)
Disclosed are compounds having the formula (I): wherein the R1, R2, R3, X, Y, A, L, and G are defined herein. These compounds bind to aspartic proteases to inhibit their activity and are useful in the treatment or amelioration of diseases associated with aspartic protease activity. Also disclosed are methods of use of the compounds of Formula I for ameliorating or treating aspartic protease related disorders in a subject in need thereof.
Pompanopeptins A and B, new cyclic peptides from the marine cyanobacterium Lyngbya confervoides
Matthew, Susan,Ross, Cliff,Paul, Valerie J.,Luesch, Hendrik
, p. 4081 - 4089 (2008/09/20)
A new 3-amino-6-hydroxy-2-piperidone (Ahp) containing peptolide, pompanopeptin A (1), and a novel N-methyl-2-amino-6-(4′-hydroxyphenyl)hexanoic acid (N-Me-Ahpha) containing cyclic pentapeptide connected with a sixth amino acid residue via a rare ureido linkage, pompanopeptin B (2), were isolated from the marine cyanobacterium Lyngbya confervoides collected from the southeastern coast of Florida. Their planar structures were determined by a combination of NMR spectroscopic analysis and mass spectrometry. The absolute configurations were established using advanced Marfey's method and chiral HPLC analysis of the chemical degradation products. Compound 1 selectively inhibited trypsin over elastase and chymotrypsin, with an IC50 value of 2.4 μM; selectivity is conferred by an arginine residue in the cyclic core.
A highly efficient method of N-methylation for the amino acid derivatives
Belagali, Shiddappa L.,Mathew, Thankamma,Himaja, M.,Kocienski, Philip
, p. 45 - 47 (2007/10/02)
Many naturally occurring, biologically active cyclic peptides are found to contain several N-methyl amino acid constituents.A method has been found out for the N-methylation of amino acid derivatives using sodium hexamethyl disilazide and methyl iodide which gives very good yield without the racemisation.
Pharmaceutical compositions containing didemnins
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, (2008/06/13)
This invention is directed to didemnin derivatives, including N-acyl congeners of didemnin A (DA); several DDB-type analogues of DA in which either pyruvic acid has been replaced (with phenylpyruvic acid or alphaketobutyric acid) or proline at position 8 has been replaced [with L-azetidine-2-carboxylic acid (AZT), L-pipecolic acid (Pip), 1-amino-1-carboxylic cyclopentane (acc 5), D-Pro or sarcosine (sar); and other cyclic depsipeptides related to the didemnins, which were isolated from a relatively polar extract of the tunicate T. solidum; namely the didemnins--X [(R)-3-hydroxy-decanoyl-(Gln) 3 -Lac-Pro didemnin A]; Y [(R)-3-hydroxy-decanoyl-(Gln) 4 -Lac-Pro didemnin A]; M (pGlu-Gln-Lac-Pro-didemnin A); N ([Tyr 5 ] didemnin B); nordidemnin N ([Tyr 5 ] nordidemnin B); and epididemnin A ([2S,4R-Hip 2 ] didemnin A).
SYNTHESIS OF CYCLO-N-METHYL-L-TYR-N-METHYL-L-TYR-D-ALA-L-ALA-O,N-DIMETHYL-L-TYR-L-ALA, A CYCLIC HEXAPEPTIDE RELATED TO THE ANTITUMOR AGENT DEOXYBOUVARDIN
Bates, Robert B.,Gin, Susan L.,Hassen, Mark A.,Hruby, Victor J.,Janda, Kim D.,et al.
, p. 785 - 790 (2007/10/02)
A synthesis of the title cyclic hexapeptide is described.Its lack of antitumor activity shows that the 14-membered ring of deoxybouvardin is needed for activity.Efforts to oxidatively its phenolic groups failed to give deoxybouvardin.
