595-39-1Relevant academic research and scientific papers
SN2 displacement at the quaternary carbon center: A novel entry to the synthesis of α,α-disubstituted α-amino acids This Letter is dedicated to the late Professor Harry Wasserman, a great chemist as well as a splendid artist
Ishihara, Kotaro,Hamamoto, Hiromi,Matsugi, Masato,Shioiri, Takayuki
supporting information, p. 3169 - 3171 (2015/05/27)
A novel method for the SN2 reaction on quaternary carbon atoms using bis(p-nitrophenyl)phosphorazidate has been developed. Chiral tertiary alcohols were directly converted into the corresponding chiral tertiary azides with complete inversion of configuration. Several α,α-disubstituted α-amino esters or amino acids were prepared through the conversion of azides to the corresponding amines by catalytic hydrogenation.
PROCESS FOR PRODUCING SOLID AMINO ACID
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Paragraph 0078; 0079, (2014/12/09)
The problem to be solved by the present invention is to ea lily and efficiently produce an amino acid having 2 to 7 carbon atoms as a high-purity solid without complicated operation, which is useful as a synthetic intermediate for medicines or agrochemicals. The present invention is characterized in comprising a step of precipitating solid amino acid with high purity. In the present invention, the by-produced salt composed of the sulfonic acid and the amine was removed to the mother liquor by reacting an amine with a sulfonic acid salt of amino acid in an aprotic polar solvent, or by reacting a sulfonic acid with an amine salt of amino acid in an aprotic polar solvent. The sulfonic acid salt of amino acid, for example, may be produced by reacting a N-(tert-butoxycarbonyl) amino acid with a sulfonic acid, or by reacting an amino acid tert-butyl ester with a sulfonic acid.
Synthesis and biological activity of nociceptin/orphanin FQ analogues substituted in position 7 or 11 with Cα,α-dialkylated amino acids
Arduin, Marika,Spagnolo, Barbara,Calo, Girolamo,Guerrini, Remo,Carra, Giacomo,Fischetti, Carmela,Trapella, Claudio,Marzola, Erika,McDonald, John,Lambert, David G.,Regoli, Domenico,Salvadori, Severo
, p. 4434 - 4443 (2008/03/13)
Previous structure-activity and NMR studies on nociceptin/orphanin FQ (N/OFQ) demonstrated that Aib substitution of Ala7 and/or Ala11 increases the peptide potency through an alpha helix structure induction mechanism. On these bases we synthesised and evaluated pharmacologically in the mouse vas deferens assay a series of N/OFQ-NH2 analogues substituted in position 7 and 11 with Cα,α-disubstituted cyclic, linear and branched amino acids. None of the 20 novel N/OFQ analogues produced better results than [Aib7]N/OFQ-NH2. Thus, this substitution was combined with other chemical modifications known to modulate peptide potency and/or efficacy generating compound 21 [Nphe1Aib7Arg14Lys15]N/OFQ-NH2 (coded as UFP-111), compound 22 [(pF)Phe4Aib7Arg14Lys15]N/OFQ-NH2 (UFP-112) and compound 23 [Phe1Ψ(CH2-NH)Gly2(pF)Phe4Aib7Arg14Lys15]N/OFQ-NH2 (UFP-113). These novel peptides behaved as highly potent NOP receptor ligands showing full (UFP-112) and partial (UFP-113) agonist and pure antagonist (UFP-111) activities in a series of in vitro functional assays performed on pharmacological preparations expressing native as well as recombinant NOP receptors.
SYNTHESIS OF α-AMINOAMIDES AND α-AMINO ACIDS FROM α-AMINONITRILES
Zil'berman, E. N.,Eremeev, I. V.,Abramov, A. V.
, p. 1243 - 1247 (2007/10/02)
The transformations of α-aminonitriles in the presence of water and manganese(IV) oxide were investigated for the case of 2-amino-2-methylpropionitrile and 2-amino-2-methylbutyronitrile.The conditions for highly selective synthesis of α-aminoamides and α-amino acids from the corresponding α-aminonitriles were determined.
