- ACE-INHIBITORS HAVING ANTIOXIDANT AND NO-DONOR ACTIVITY
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Multifonctional ACE inhibitor compounds are provided, that combine ACE-inhibiting activity with capability to scavenge superoxide and other reactive oxygen species, and that may further function as nitric oxide donors. The compounds are useful for preventing or treating various disorders, including cardiovascular, and diabetes associated disorders.
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Page/Page column 57; 59
(2010/02/07)
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- Utility of tetrathiomolybdate and tetraselenotungstate: Efficient synthesis of cystine, selenocystine, and their higher homologues
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Efficient synthesis of cystine, selenocystine, and their higher homologues like homo and bishomo amino acid derivatives from natural amino acid derivatives using tetrathiomolybdate and tetraselenotungstate reagents under mild and neutral conditions is reported. The generality of the reaction has been studied by capping various groups to amino and carboxyl components of canonical amino acids.
- Bhat, Ramakrishna G.,Porhiel, Emmanuel,Saravanan, Vadivelu,Chandrasekaran, Srinivasan
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p. 5251 - 5253
(2007/10/03)
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- N-Me-pAB-Glu-γ-Glu-γ-Tyr(3-NO2): An internally quenched fluorogenic γ-glutamyl hydrolase substrate
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A γ-glutamyl tripeptide containing an internally quenched fluorophore has been synthesized and shown to be a substrate for recombinant rat γ-glutamyl hydrolase. HPLC, LC-MS, and fluorescence spectra support the conclusion that selective hydrolysis occurs
- Pankuch, Jessica J.,Coward, James K.
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p. 1561 - 1564
(2007/10/03)
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- Total synthesis of the methanogenic cofactors methanofuran and methanofuran b
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Methanofuran, 3-[p-((N-(N″-((4R,5S)- or (4S,5A)-4,5,7-tricarboxyheptanoyl)-γL-glutamyl-γ-L-glutamyl)-β- amino)ethyl]phenoxymethyl}-5-(aminomethyl)furan, and methanofuran b, 3-{p-[(N-(-γ-L-glutamyl-γ-L-glutamyl-γ-L-glutamyl-γ-L- glutamyl)-β-amino)ethyl]phenoxymethyl}-5-(aminomethyl)furan, are the first cofactors involved in the conversion of carbon dioxide to methane by the methanogenic bacteria Methanobacterium thermoautotrophicum and Methanosarcina barkeri, respectively. These two cofactors have now been synthesized, starting from glutamic acid, dimethyl glutarate, methyl 5-formyl-3-furoate, and tyramine. The synthetic compounds give the same NMR and mass spectra and biological activities as the natural cofactors.
- Sullins, David W.,Bobik, Thomas A.,Wolfe, Ralph S.,Rinehart, Kenneth L.
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p. 6646 - 6651
(2007/10/02)
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- Synthesis and Siderophore Activity of Albomycin-like Peptides Derived from N5-Acetyl-N5-hydroxy-L-ornithine
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N5-Acetyl-N5-hydroxy-L-ornithine (1), the key constituent of several microbial siderophores, has been synthesized in 23percent yield overall from N-Cbz-L-glutamic acid 1-tert-butyl ester (6) derived from L-glutamic acid.Reduction of 6 to 7 and treatment with N-(trichloroethoxy)carbonyl>-O-benzylhydroxylamine (8), and diethyl azodicarboxylate and triphenylphosphine followed by deprotection produced the protected N5-acetyl-N5-hydroxy-L-ornithine derivatives 11 and 12 in large quantities (10-20 g).Following α-amino and α-carboxyl deprotections of 11 and 12, EEDQ mediated peptide coupling and final deprotection provided amino acid 1 and six albomycin-like peptides (20, 23, 25, 28, 35, and 36).The growth-promoting ability of each was evaluated with the siderophore biosynthesis mutant Shigella flexneri SA240 (SA 100 iucD:Tn5).These results indicate that substantial modification of the framework of peptide-based siderophores can be tolerated by microbial iron-transport systems.
- Dolence, E. Kurt,Lin, Chia-En,Miller, Marvin J.,Payne, Shelley M.
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p. 956 - 968
(2007/10/02)
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- 1-Hydroxy-3-amino-2-piperidone (δ-N-Hydroxycycloornithine) Derivatives: Key Intermediates for the Synthesis of Hydroxamate-Based Siderophores
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Several routes for the synthesis of δ-N-(benzyloxy)cycloornithine (2) from glutamic acid derived starting materials are described.Efficient methods were developed for the synthesis of glutamic acid γ-semialdehyde and γ-hydroxynorvaline derivatives as key substrates for the preparation of δ-N-hydroxyornithine analogues.Thus, the best approaches to the synthesis of 2 were: (1) reductive cyclization of an N-hydroxysuccinimide ester of the O-benzyloxime 4 of α-amino-protected glutamic acid γ-semialdehyde 5 and (2) cyclization of the N-(benzyloxy)amide of δ-bromonorvaline (7).
- Kolasa, Teodozyj,Miller, Marvin J.
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p. 1711 - 1721
(2007/10/02)
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