Total Synthesis and Structural Revision of Aeruginosin KT608A.

The synthesis of the presumed structure of aeruginosin KT608A was accomplished for the first time. The unusual d-diepi-Choi core was prepared from tyrosine via C-H activation and heterogeneous hydrogenation. Due to differences in the spectral data of synthetic and natural samples, a revised structure featuring l-diepi-Choi was proposed, which was synthesized and confirmed to be identical. On the basis of these findings, revised structures for six additional aeruginosins (KT608B, KT650, GH553, DA495A, DA511, and KB676) are presented.

[1]  K. Gademann,et al.  Investigating the Toxicity of the Aeruginosin Chlorosulfopeptides by Chemical Synthesis. , 2016, Angewandte Chemie.

[2]  Grégory Danoun,et al.  Divergent Synthesis of Aeruginosins Based on a C(sp(3))-H Activation Strategy. , 2015, Chemistry.

[3]  Grégory Danoun,et al.  A general and scalable synthesis of aeruginosin marine natural products based on two strategic C(sp³)-H activation reactions. , 2015, Angewandte Chemie.

[4]  S. Carmeli,et al.  New Prenylated Aeruginosin, Microphycin, Anabaenopeptin and Micropeptin Analogues from a Microcystis Bloom Material Collected in Kibbutz Kfar Blum, Israel , 2015, Marine drugs.

[5]  B. Li,et al.  Palladium-catalyzed C-7 alkenylation of indolines using molecular oxygen as the sole oxidant , 2015 .

[6]  K. Gademann,et al.  The toxicity and enzyme activity of a chlorine and sulfate containing aeruginosin isolated from a non-microcystin-producing Planktothrix strain. , 2014, Harmful algae.

[7]  E. Carreira,et al.  Access to the aeruginosin serine protease inhibitors through the nucleophilic opening of an oxabicyclo[2.2.1]heptane: total synthesis of microcin SF608. , 2014, Chemistry.

[8]  S. Carmeli,et al.  Protease inhibitors from Microcystis aeruginosa bloom material collected from the Dalton Reservoir, Israel. , 2013, Journal of natural products.

[9]  T. Mei,et al.  Synthesis of indolines via Pd(II)-catalyzed amination of C-H bonds using PhI(OAc)2 as the bystanding oxidant. , 2013, Organic letters.

[10]  B. Trost,et al.  Total synthesis of aeruginosin 98B. , 2012, Journal of the American Chemical Society.

[11]  S. Carmeli,et al.  Metabolites of Microcystis aeruginosa bloom material from Lake Kinneret, Israel. , 2012, Journal of natural products.

[12]  E. Carreira,et al.  Synthesis of Microcin SF608 through nucleophilic opening of an oxabicyclo[2.2.1]heptane. , 2010, Organic letters.

[13]  M. Fushimi,et al.  Synthesis of hydroxylated bicyclic amino acids from L-tyrosine: octahydro-1H-indole carboxylates. , 2008, The Journal of organic chemistry.

[14]  J. D. Del Valle,et al.  Chemistry and biology of the aeruginosin family of serine protease inhibitors. , 2008, Angewandte Chemie.

[15]  N. Blomberg,et al.  Total synthesis and structural confirmation of chlorodysinosin A. , 2006, Journal of the American Chemical Society.

[16]  F. Sarabia,et al.  Stereoselective synthesis of E-64 and related cysteine proteases inhibitors from 2,3-epoxyamides. , 2005, Bioorganic & medicinal chemistry.

[17]  S. Hanessian,et al.  The N-acyloxyiminium ion aza-Prins route to octahydroindoles: total synthesis and structural confirmation of the antithrombotic marine natural product oscillarin. , 2004, Journal of the American Chemical Society.

[18]  M. Vallribera,et al.  Synthesis of the proposed core of aeruginosins 205: the new α-amino acid (2S,3aS,6R,7aS)-2-carboxy-6-chlorooctahydroindole , 2003 .

[19]  S. Carmeli,et al.  Syntheses of both the putative and revised structures of aeruginosin EI461 bearing a new bicyclic alpha-amino acid. , 2003, Organic letters.

[20]  S. Hanessian,et al.  Total synthesis and structural confirmation of the marine natural product Dysinosin A: a novel inhibitor of thrombin and Factor VIIa. , 2002, Journal of the American Chemical Society.

[21]  S. Carmeli,et al.  Three novel protease inhibitors from a natural bloom of the cyanobacterium Microcystis aeruginosa. , 2002, Journal of natural products.

[22]  M. López-Canet,et al.  Synthesis of microcin SF608. , 2002, The Journal of organic chemistry.

[23]  Roger A. Moore,et al.  Synthesis and Evaluation of Alternative Substrates for Arginasease , 2002 .

[24]  N. Valls,et al.  First total syntheses of aeruginosin 298-A and aeruginosin 298-B, based on a stereocontrolled route to the new amino acid 6-hydroxyoctahydroindole-2-carboxylic acid. , 2001, Chemistry.

[25]  P. Wipf,et al.  Total synthesis and stereochemical revision of (+)-aeruginosin 298-A. , 2000, Organic letters.

[26]  M. López-Canet,et al.  Total Synthesis and Reassignment of Configuration of Aeruginosin 298-A , 2000 .

[27]  G. Giacomelli,et al.  4-(4,6-Dimethoxy[1,3,5]triazin-2-yl)-4-methyl-morpholinium Chloride (DMTMM): A Valuable Alternative to PyBOP for Solid Phase Peptide Synthesis , 2000 .

[28]  K. Yamaguchi,et al.  Aeruginosin 298-A, a thrombin and trypsin inhibitor from the blue-green alga Microcystis aeruginosa (NIES-298) , 1994 .