메뉴 건너뛰기




Volumn 11, Issue 8, 2005, Pages 472-480

Kinetic and mechanistic investigation of the selective acidolysis of the C-terminal amide bond of N-acyl-N,α,α-trialkyl glycine amides

Author keywords

N acyl N (4 methoxybenzyl) , trialkyl glycine amides; Oxazolonium salts; Rate constants; Reaction mechanism; Selective acidolysis; Ugi Passerini adducts

Indexed keywords

AMIDE; AMINO ACID; GLYCINAMIDE;

EID: 23144461475     PISSN: 10752617     EISSN: None     Source Type: Journal    
DOI: 10.1002/psc.640     Document Type: Article
Times cited : (8)

References (13)
  • 2
    • 0141899806 scopus 로고    scopus 로고
    • Aminopeptidase M seems to jump over peptide bonds formed by N-terminal α,α-disubstituted amino acids
    • Bajusz S, Hudecz F (eds). Akadémiai Kiadó: Budapest
    • Medzihradszky-Schweiger H, Medzihradszky K, Nádasi H, Suli-Vargha H. Aminopeptidase M seems to jump over peptide bonds formed by N-terminal α,α-disubstituted amino acids. In Peptides 1998, Bajusz S, Hudecz F (eds). Akadémiai Kiadó: Budapest, 1999; 606-607.
    • (1999) Peptides 1998 , pp. 606-607
    • Medzihradszky-Schweiger, H.1    Medzihradszky, K.2    Nádasi, H.3    Suli-Vargha, H.4
  • 3
    • 0001023731 scopus 로고
    • N-Methylamino acids in peptide synthesis. II. A new synthesis of N-benzyloxycarbonyl, N-methylamino acids
    • McDermot JR, Benoiton NC. N-Methylamino acids in peptide synthesis. II. A new synthesis of N-benzyloxycarbonyl, N-methylamino acids. Can. J. Chem. 1973; 51: 1915-1919.
    • (1973) Can. J. Chem. , vol.51 , pp. 1915-1919
    • McDermot, J.R.1    Benoiton, N.C.2
  • 6
    • 37049133131 scopus 로고
    • Polypeptides. Part XXIII. The synthesis of peptides of α-benzylphenylalanine by unconventional methods, with a note on magnetic non-equivalence in derivatives of α-benzylphenylalanine
    • Maia HL, Ridge B, Rydon HN. Polypeptides. Part XXIII. The synthesis of peptides of α-benzylphenylalanine by unconventional methods, with a note on magnetic non-equivalence in derivatives of α-benzylphenylalanine. J. Chem. Soc. 1973; 98-105.
    • (1973) J. Chem. Soc. , pp. 98-105
    • Maia, H.L.1    Ridge, B.2    Rydon, H.N.3
  • 7
    • 23144438455 scopus 로고
    • Facilitation of oxazolinone formation by bulky amino acid side chains
    • Jung G, Bayer E (eds). Walter de Gruyter: Berlin
    • Freitas AM, Maia HLS. Facilitation of oxazolinone formation by bulky amino acid side chains. In Peptides 1988, Jung G, Bayer E (eds). Walter de Gruyter: Berlin, 1989; 13-15.
    • (1989) Peptides 1988 , pp. 13-15
    • Freitas, A.M.1    Maia, H.L.S.2
  • 9
    • 0141905834 scopus 로고    scopus 로고
    • An improved approach for the synthesis of α,α-dialkyl glycines derivatives by the Ugi-Passerini reaction
    • Costa SPG, Maia HLS, Pereira-Lima SMMA. An improved approach for the synthesis of α,α-dialkyl glycines derivatives by the Ugi-Passerini reaction. Org. Biomol. Chem. 2003; 1: 1475-1479.
    • (2003) Org. Biomol. Chem. , vol.1 , pp. 1475-1479
    • Costa, S.P.G.1    Maia, H.L.S.2    Pereira-Lima, S.M.M.A.3
  • 10
    • 0344981503 scopus 로고    scopus 로고
    • Synthesis of N-acyl-N,α,α-trialkyl and N-acyl-α,α-dialkyl glycines by selective cleavage of Ugi-Passerini adducts. Qualitative assessment of the effect of substituents on the path and yield of reaction
    • Jiang W-Q, Costa SPG, Maia HLS. Synthesis of N-acyl- N,α,α-trialkyl and N-acyl-α,α-dialkyl glycines by selective cleavage of Ugi-Passerini adducts. Qualitative assessment of the effect of substituents on the path and yield of reaction. Org. Biomol. Chem. 2003; 1: 3804-3810.
    • (2003) Org. Biomol. Chem. , vol.1 , pp. 3804-3810
    • Jiang, W.-Q.1    Costa, S.P.G.2    Maia, H.L.S.3
  • 11
    • 37049087217 scopus 로고
    • A reversible protecting group for the amide bond in peptides - Use in the synthesis of difficult sequences
    • Johnson T, Quibell M, Owen D, Sheppard RC. A reversible protecting group for the amide bond in peptides - use in the synthesis of difficult sequences. J. Chem. Soc. Chem. Commun. 1993; 369-372.
    • (1993) J. Chem. Soc. Chem. Commun. , pp. 369-372
    • Johnson, T.1    Quibell, M.2    Owen, D.3    Sheppard, R.C.4
  • 13
    • 0043287137 scopus 로고    scopus 로고
    • Synthesis of 1-(m-hydroxybenzyl)-substituted 1,2,3,4-tetrahydroiso-quinoline3-carboxylic acid derivatives as opioid peptide mimetics - Unexpected amide bond cleavages under mild conditions
    • Mannekens E, Crisma M, Van Cauwenberghe S, Tourwé D. Synthesis of 1-(m-hydroxybenzyl)-substituted 1,2,3,4-tetrahydroiso-quinoline3-carboxylic acid derivatives as opioid peptide mimetics - unexpected amide bond cleavages under mild conditions. Eur. J. Org. Chem. 2003; 3300-3307.
    • (2003) Eur. J. Org. Chem. , pp. 3300-3307
    • Mannekens, E.1    Crisma, M.2    Van Cauwenberghe, S.3    Tourwé, D.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.