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Volumn 76, Issue 9, 2011, Pages 3166-3173

Giant macrolactams based on β-sheet peptides

Author keywords

[No Author keywords available]

Indexed keywords

AQUEOUS SOLUTIONS; CHLORIDE RESIN; DEPROTECTION; LINEAR PEPTIDES; MACRO-CYCLIZATION; MACROCYCLES; NATURAL AMINO ACIDS; NMR STUDIES; SHEET STRUCTURE; SOLID PHASE PEPTIDE SYNTHESIS; TRIPEPTIDE;

EID: 79955567720     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo102598n     Document Type: Article
Times cited : (13)

References (55)
  • 15
    • 79955558455 scopus 로고    scopus 로고
    • Robinson, J. A. Science 2010, 327, 1010-1013
    • (2010) Science , vol.327 , pp. 1010-1013
    • Robinson, J.A.1
  • 43
    • 79955568650 scopus 로고    scopus 로고
    • note
    • Most standard peptide synthesis procedures followed those in the "Synthesis Notes" section of the 2009/2010 Novabiochem catalog.
  • 44
    • 0034674535 scopus 로고    scopus 로고
    • Either Fmoc*-Hao-OH or Fmoc-Hao-OH was used to introduce the Hao residue. Fmoc*-Hao-OH has been described previously in ref 10b. Fmoc* refers to the 2,7-di- tert -butyl-Fmoc group. This more soluble analogue of the Fmoc group is described in: Stigers, K. D.; Koutroulis, M. R.; Chung, D. M.; Nowick, J. S. J. Org. Chem. 2000, 65, 3858-3860 For details of the preparation of Fmoc-Hao-OH, see the Supporting Information.
    • (2000) J. Org. Chem. , vol.65 , pp. 3858-3860
    • Stigers, K.D.1    Koutroulis, M.R.2    Chung, D.M.3    Nowick, J.S.4
  • 48
    • 79955568312 scopus 로고    scopus 로고
    • note
    • In the cyclization step, most macrocyclic peptides were synthesized using HCTU/DIEA/DMF. Cyclization using HCTU/DIEA/DMF produces yellowish impurities that remain after deprotection with TFA. When these colored impurities proved difficult to remove by HPLC purification, cyclization was alternatively performed with HBTU/HOBt/N-methylmorpholine/DMF. (15)
  • 49
    • 79955564570 scopus 로고    scopus 로고
    • note
    • HPLC analysis of cyclic peptide 8a shows comparable purities of the crude products from cyclization at 0.5 and 10 mM concentrations, indicating that macrocyclization causes no or little polymerization. For details, see Figure S1 in the Supporting Information. If polymers or oligomers were to form under these conditions, the HPLC traces from cyclization at 10 mM would show impurities substantially greater than those at 0.5 mM.
  • 51
    • 79955554019 scopus 로고    scopus 로고
    • note
    • NOEs between the two Hao units cannot be observed due to symmetry.
  • 52
    • 79955556692 scopus 로고    scopus 로고
    • note
    • 2O, and the NOEs involving these protons cannot be observed under the conditions of the ROESY experiments.
  • 55
    • 79955553215 scopus 로고    scopus 로고
    • note
    • δOrn value of 1.3 ppm in a chloroform solution. For details, see ref 10c.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.