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Volumn , Issue 35, 2008, Pages 5936-5945

Manufacturing and PEGylation of a dual-acting peptide for diabetes

Author keywords

Fragment synthesis; Mixed phase synthesis; Peptides; Solid phase synthesis; Synthesis design

Indexed keywords


EID: 56749168209     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200800722     Document Type: Article
Times cited : (3)

References (34)
  • 1
    • 56749172165 scopus 로고    scopus 로고
    • For recent reviews on GLP-1, see: a A. P. Abhay, D. M. Ravichand, V. Seshayamma, C. P. Satish, Int. J. Endocrinol. Metab. 2006, 4, 151-166;
    • For recent reviews on GLP-1, see: a) A. P. Abhay, D. M. Ravichand, V. Seshayamma, C. P. Satish, Int. J. Endocrinol. Metab. 2006, 4, 151-166;
  • 9
    • 56749117513 scopus 로고    scopus 로고
    • See, for instance:, Eds, H. Baltes, W. Göpel, J. Hesse, CRC Press Taylor & Francis Group, Boca Raton
    • a) See, for instance: N. L. Benoiton, Chemistry of Peptide Synthesis Sensors Update (Eds.: H. Baltes, W. Göpel, J. Hesse), CRC Press Taylor & Francis Group, Boca Raton, 2006 pp. 125-154;
    • (2006) Chemistry of Peptide Synthesis Sensors Update , pp. 125-154
    • Benoiton, N.L.1
  • 15
    • 56749140456 scopus 로고    scopus 로고
    • E. Atherton, R. Berry, D. Simpkin, D. Wellings, C. Willis, J. A. Eriksen, S. Buoen, Innovation and Perspectives in Solid Phase Synthesis & Combinatorial Libraries: Peptides, Proteins and Nucleic Acids-Small Molecule Organic Chemistry Diversity, Collected Papers, International Symposium, 6th, York, United Kingdom, Aug. 31-Sept. 4 1999, 2001;
    • d) E. Atherton, R. Berry, D. Simpkin, D. Wellings, C. Willis, J. A. Eriksen, S. Buoen, Innovation and Perspectives in Solid Phase Synthesis & Combinatorial Libraries: Peptides, Proteins and Nucleic Acids-Small Molecule Organic Chemistry Diversity, Collected Papers, International Symposium, 6th, York, United Kingdom, Aug. 31-Sept. 4 1999, 2001;
  • 20
    • 56749115538 scopus 로고    scopus 로고
    • 31 partially underwent side reactions during SPPS via a dehydroalanine intermediate, which was formed by S-trityl elimination. In particular, this undesired side reaction was found during treatment with base, for example, during piperidine-mediated Fmoc deprotection.
    • 31 partially underwent side reactions during SPPS via a dehydroalanine intermediate, which was formed by S-trityl elimination. In particular, this undesired side reaction was found during treatment with base, for example, during piperidine-mediated Fmoc deprotection.
  • 21
    • 56749092726 scopus 로고    scopus 로고
    • Fmoc-Cys(Trt)OtBu has been described previously: L. Chen, N. Fotouhi, D. Y. Jackson, J. Tilley, WO 00/63234, 2000
    • Fmoc-Cys(Trt)OtBu has been described previously: L. Chen, N. Fotouhi, D. Y. Jackson, J. Tilley, WO 00/63234, 2000.
  • 26
    • 2442650736 scopus 로고    scopus 로고
    • See, for instance a, Eds, K. C. Nicolaou, R. Hanko, W. Hartwig, Wiley-VCH, Weinheim
    • See, for instance a) S. Bräse, S. Dahmen in Handbook of Combinatorial Chemistry (Eds.: K. C. Nicolaou, R. Hanko, W. Hartwig), Wiley-VCH, Weinheim, 2002, pp. 59-169;
    • (2002) Handbook of Combinatorial Chemistry , pp. 59-169
    • Bräse, S.1    Dahmen, S.2
  • 30
    • 56749137887 scopus 로고    scopus 로고
    • The alkylation site has not yet been determined. We assume that Cys, Tyr or Trp are alkylated
    • The alkylation site has not yet been determined. We assume that Cys, Tyr or Trp are alkylated.
  • 32
    • 56749133828 scopus 로고    scopus 로고
    • The yield includes the peptide content of the starting peptide (approx. 80%), which contains stabilizing salts and residual water. Additionally, the indicated weight is based on the peptide portion disregarding the PEG portion.
    • The yield includes the peptide content of the starting peptide (approx. 80%), which contains stabilizing salts and residual water. Additionally, the indicated weight is based on the peptide portion disregarding the PEG portion.
  • 33
    • 56749094812 scopus 로고    scopus 로고
    • A portion of the toluene solution was evaporated to dryness, and the residue was analyzed (HPLC method B). Accordingly, the ester was formed with complete retention of the stereogenic centre (99.8%ee).
    • A portion of the toluene solution was evaporated to dryness, and the residue was analyzed (HPLC method B). Accordingly, the ester was formed with complete retention of the stereogenic centre (99.8%ee).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.