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Volumn 4, Issue 8, 1998, Pages 1570-1580

Solid-phase syntheses of peptoids using Fmoc-protected N-substituted glycines: The synthesis of (retro)peptoids of leu-enkephalin and substance P

Author keywords

Mass spectrometry; Peptidomimetics; Peptoids; Solid phase synthesis; Substance P

Indexed keywords

GLYCINE; LEUCINE ENKEPHALIN; PEPTOID; RETROPEPTOID; SUBSTANCE P;

EID: 0031875776     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(19980807)4:8<1570::AID-CHEM1570>3.0.CO;2-2     Document Type: Article
Times cited : (107)

References (46)
  • 1
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    • A. Giannis, T. Kolter, Angew. Chem. 1993, 105, 1303-1326; Angew. Chem. Int. Ed. Engl. 1993, 32, 1244-1267.
    • (1993) Angew. Chem. , vol.105 , pp. 1303-1326
    • Giannis, A.1    Kolter, T.2
  • 2
    • 33745502124 scopus 로고
    • A. Giannis, T. Kolter, Angew. Chem. 1993, 105, 1303-1326; Angew. Chem. Int. Ed. Engl. 1993, 32, 1244-1267.
    • (1993) Angew. Chem. Int. Ed. Engl. , vol.32 , pp. 1244-1267
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    • H. Kessler, Angew. Chem. 1993, 105, 512-513; Angew. Chem. Int. Ed. Engl. 1993, 32, 543-544.
    • (1993) Angew. Chem. , vol.105 , pp. 512-513
    • Kessler, H.1
  • 5
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    • H. Kessler, Angew. Chem. 1993, 105, 512-513; Angew. Chem. Int. Ed. Engl. 1993, 32, 543-544.
    • (1993) Angew. Chem. Int. Ed. Engl. , vol.32 , pp. 543-544
  • 18
    • 3542991631 scopus 로고    scopus 로고
    • Thesis, Utrecht University, The Netherlands.
    • 1 Antagonists, Thesis, Utrecht University, The Netherlands. 1997.
    • (1997) 1 Antagonists
    • Boks, G.J.1
  • 28
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    • note
    • The nomenclature is according to the proposed nomenclature by Simon et al. (ref. [2]). For the one letter code of amino acids, we have proposed the prefix n; thus for example nY, nF, and nL; see ref. [8a].
  • 34
    • 3543008504 scopus 로고    scopus 로고
    • note
    • It was found that intramolecular aminolysis, that is, diketopiperazine formation was a serious by-reaction of a dipeptoid connected to TentaGel® SOH by an ester linkage. The use of Rink amide resin (TentalGel® S RAM), for the preparation of (peptoid) amides, entirely circumvented the problem of diketopiperazine formation.
  • 37
    • 3543030019 scopus 로고    scopus 로고
    • note
    • a) This protection does appear to be sufficient to mask the nucleophilicity of the guanidino function. Ornithine formation through acylation of the unprotected ω-nitrogen during coupling and subsequent intramolecular decomposition during deprotection is completely avoided;
  • 40
    • 3542997625 scopus 로고    scopus 로고
    • The peptide was acetylated to facilitate purification
    • The peptide was acetylated to facilitate purification.
  • 43
    • 3543005505 scopus 로고    scopus 로고
    • note
    • For storage, the hydrochloride salt was prepared by dissolving the ester in ether followed by precipitation with a saturated solution of HCl in ether.
  • 46
    • 0038942328 scopus 로고
    • June Mode 433A Peptide Synthesizer
    • Applied Biosystems Research News June 1993, Mode 433A Peptide Synthesizer, 1-12.
    • (1993) Applied Biosystems Research News , pp. 1-12


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.