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Volumn , Issue 22, 2000, Pages 3755-3761

Synthesis of the novel amino acid 4-amino-3-(aminomethyl)benzoic acid (AmAbz) and its protected derivatives as building blocks for pseudopeptide synthesis

Author keywords

Amidoalkylation; Combinatorial chemistry; Peptidomimetics; Scaffold; Solid phase synthesis

Indexed keywords

4 AMINO 3 (AMINOMETHYL)BENZOIC ACID (9 FLUORENYLMETHYLCARBONYL); 4 AMINO 3 (AMINOMETHYL)BENZOIC ACID (BUTYLOXYCARBONYL); 4 AMINO 3 (AMINOMETHYL)BENZOIC ACID DERIVATIVE; 9 FLUORENYLMETHYLCARBONYL ALANYLPHENYALANYL 4 AMINO 3 (AMINOMETHYL)BENZOIC ACID (HYDROGEN LYSYLLEUCINE)VALYLGLYCINAMIDE; AMINO ACID DERIVATIVE; BENZOIC ACID DERIVATIVE; CYANAMIDE; PSEUDOPEPTIDE; UNCLASSIFIED DRUG;

EID: 0033709871     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200011)2000:22<3755::aid-ejoc3755>3.0.co;2-i     Document Type: Article
Times cited : (8)

References (40)
  • 4
    • 84987566762 scopus 로고
    • Abbreviations for AmAbz derivatives are constructed according to the recommendations of the IUPAC-IUB Commission on Biochemical Nomenclature (Eur. J. Biochem. 1984, 138, 9-37), 4-amino and 3-aminomethyl groups being defined as main-chain and side-chain groups, respectively. Additional abbreviations used are: - Boc: tert-butyloxycarbonyl; BOP: benzotriazol-1-yloxy-tris(dimethylamino)-phosphonium hexafluorophosphate; DIC: N,N′-diisopropylcarbodiimide; DMF: N,N-dimethylformamide; DIEA: N-ethyldiisopropylamine; HOBt: N-hydroxybenzotriazole; Pht: phthaloyl; OSu: succinimidyloxy; TFA: trifiuoroacetic acid.
    • (1984) Eur. J. Biochem , vol.138 , pp. 9-37
  • 16
    • 0003033095 scopus 로고
    • Ed.: J. Zabicky, Interscience Publishers, London
    • R. B. Homer, C. D. Johnson, in: The Chemistry of Amides (Ed.: J. Zabicky), Interscience Publishers, London, 1970; pp. 187-245.
    • (1970) The Chemistry of Amides , pp. 187-245
    • Homer, R.B.1    Johnson, C.D.2
  • 21
    • 33847561258 scopus 로고    scopus 로고
    • note
    • In preliminary experiments, acid hydrolysis turned out to be impracticable due to a very sluggish process even in hot concentrated acid.
  • 23
    • 33847543722 scopus 로고    scopus 로고
    • note
    • Prior conversion of carboxyl group into methyl ester was achieved in order to avoid any side reaction with carbonyldiimidazole.
  • 24
    • 85088004859 scopus 로고    scopus 로고
    • note
    • [9]
  • 28
    • 85088005525 scopus 로고    scopus 로고
    • note
    • 2 to give peptide resin 12, solvent (DCM or DMF) was added 5 min after carbodiimide addition for technical reasons (gelation of the reaction medium, probably due to precipitation of Fmoc-Phe symmetrical anhydride).
  • 30
    • 85088005236 scopus 로고    scopus 로고
    • note
    • [6]).
  • 31
    • 85088005618 scopus 로고    scopus 로고
    • note
    • 2.
  • 32
    • 33947338256 scopus 로고
    • An explanation of this efficiency is that the effective acylating species may be the initially formed O-acylisourea intermediate, since the arylamine is a stronger nucleophile than neutral carboxylic acid and, thus, acylation may have occurred before the symmetrical anhydride had formed. This interpretation is consistent with the proposal of direct formation of acylpyridinium from O-acylisourea and pyridine (D. F. DeTar, R. Silverstein, J. Am. Chem. Soc. 1966, 88, 1020-1023). In addition, since the poorly nucleophilic arylamino group of AmAbz is not protonated in the medium, it is able to react in the absence of base.
    • (1966) J. Am. Chem. Soc. , vol.88 , pp. 1020-1023
    • DeTar, D.F.1    Silverstein, R.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.