- Thermal Syntheses of Polypeptides from N-Boc-Amino Acid(Aspartic Acid,β-Aminoglutaric Acid) Anhydrides
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N-t-Butyloxycarbonyl-amino acid(aspartic acid:Asp, glutamic acid:Glu, β-aminoglutaric acid: β-Agl)anhydrides were deprotected upon heating at temperatures slightly higher than the melting points of these compounds and polypeptides were synthesized easily in high yield.
- Munegumi, Toratane,Meng, Yan-Quing,Harada, Kaoru
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- CRYSTALLINE FORMS OF A PYRROLIDONE DERIVATIVE USEFUL IN THE TREATMENT OF ALZHEIMER'S DISEASE AND PREPARATION THEREOF
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The present invention provides processes to manufacture crystalline N-[(3S)-1-[4-[(3-fluorophenyl)methoxy]phenyl]-5-oxo-pyrrolidin-3-yl]acetamide. Also disclosed are polymorphic forms of said compound as well as compounds useful as intermediates in the methods of the invention.
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Page/Page column 18; 19
(2015/05/19)
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- Polypeptide formation by heating N-t-butyloxycarbonyl acidic amino acid derivatives
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An acid labile N-protecting group for amino acids, t-butyloxycarbonyl (Boc) group has deprotected at elevated temperatures. The study describes an application of the lability on heating to synthesis of polypeptides from acidic amino acids. t-Butyloxycarbonyl-acidic amino acids (aspartic acid, glutamic acid and β-aminoglutaric acid) and their anhydrides were heated at the higher temperatures than their melting points. Anhydrides of t-butyloxycarbonyl-aspartic acid and t-butyloxycarbonyl-β-aminoglutaric acid gave polypeptides. Thermal analyses of the substrates clarified the pathway of the polypeptide formation.
- Munegumi,Qing Meng,Harada
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p. 4716 - 4722
(2014/12/10)
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- Isoform-selective thiazolo[5,4-b]pyridine S1P1 agonists possessing acyclic amino carboxylate head-groups
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Replacement of the azetidine carboxylate of an S1P1 agonist development candidate, AMG 369, with a range of acyclic head-groups led to the identification of a novel, S1P3-sparing S1P1 agonist, (-)-2-amino -4-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl) phenyl)-2-methylbutanoic acid (8c), which possessed good in vivo efficacy and pharmacokinetic properties. A 0.3 mg/kg oral dose of 8c produced a statistically significant reduction in blood lymphocyte counts 24 h post-dosing in female Lewis rats.
- Reed, Anthony B.,Lanman, Brian A.,Neira, Susana,Harrington, Paul E.,Sham, Kelvin K.C.,Frohn, Mike,Pickrell, Alexander J.,Tasker, Andrew S.,Gore, Anu,Fiorino, Mike,Itano, Andrea,McElvain, Michele,Middleton, Scot,Morrison, Henry,Xu, Han,Xu, Yang,Wong, Min,Cee, Victor J.
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supporting information; scheme or table
p. 1779 - 1783
(2012/04/04)
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- Bronsted base-assisted boronic acid catalysis for the dehydrative intramolecular condensation of dicarboxylic acids
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Bronsted base-assisted boronic acid catalysis for the dehydrative self-condensation of carboxylic acids is described. Arylboronic acid bearing bulky (N,N-dialkylamino)methyl groups at the 2,6-positions can catalyze the intramolecular dehydrative condensation of di-and tetracarboxylic acids. This is the first successful method for the catalytic dehydrative self-condensation of carboxylic acids.(Figure Presented)
- Sakakura, Akira,Ohkubo, Takuro,Yamashita, Risa,Akakura, Matsujiro,Ishihara, Kazuaki
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scheme or table
p. 892 - 895
(2011/05/02)
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- An unexpected product from attempted reductive etherification of a silyl alcohol with an aldehyde
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Reductive etherification, using BiBr3/Et3SiH, between two modified amino acids, one with a silyl alcohol side chain and one with an aldehyde side chain, gave, not the desired bis-amino acid, but a tetrahydrooxazine, in good yield.
- White, Christopher G.H.,Tabor, Alethea B.
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p. 6932 - 6937
(2008/02/11)
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- A new entry to polyfunctionalized 4,5-trans disubstituted oxazolidin-2-ones from L-aspartic acid
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A straightforward synthesis of enantiomerically pure (4R,5S)-5-oxazolidinecarboxylic acid, 2-oxo-4-[(t-butyldimethyl-silyloxy)methyl]-, benzyl ester and of (4S,5S)-4-oxazolidinecarboxylic acid, 2-oxo-5-[(t-butyldimethylsilyloxy)methyl]-, benzyl ester was envisaged starting from readily available L-aspartic acid. The key step is the diastereoselective addition of iodine with the introduction of a new stereogenic centre.
- Luppi, Gianluigi,Tomasini, Claudia
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p. 797 - 800
(2007/10/03)
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