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Volumn 10, Issue 3, 2004, Pages 617-626

α,α-Disubstituted Glycines Bearing a Large Hydrocarbon Ring: Peptide Self-Assembly through Hydrophobic Recognition

Author keywords

Amino acids; Peptides; Protein design; Ring closing metathesis; Self assembly

Indexed keywords

AMINES; CARBOXYLIC ACIDS; DERIVATIVES; HYDROCARBONS; HYDROPHOBICITY; OLEFINS; SEDIMENTATION; SELF ASSEMBLY; SYNTHESIS (CHEMICAL);

EID: 1242330387     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200305492     Document Type: Article
Times cited : (17)

References (50)
  • 27
    • 0000785058 scopus 로고    scopus 로고
    • c) review: A. Fürstner, Angew. Chem. 2000, 112, 3140-3172; Angew. Chem. Int. Ed. 2000, 39, 3012-3043;
    • (2000) Angew. Chem. , vol.112 , pp. 3140-3172
    • Fürstner, A.1
  • 28
    • 0001399412 scopus 로고    scopus 로고
    • c) review: A. Fürstner, Angew. Chem. 2000, 112, 3140-3172; Angew. Chem. Int. Ed. 2000, 39, 3012-3043;
    • (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 3012-3043
  • 31
    • 1242315289 scopus 로고    scopus 로고
    • note
    • Direct dialkenylation of dimethylmalonate (4a) in the presence of an excess amount of a base (5 equiv Na in methanol) and allyl bromide (5 equiv) resulted in the formation of the monoallyl malonate (55 % yield), together with some diallyl malonate (12 % yield).
  • 38
    • 1242337880 scopus 로고    scopus 로고
    • note
    • This phenomenon is also seen with acyclic long aliphatic substituents at the α position. In the case of n-propyl disubstitution (13a), the intermediate isocyanate (15a) can react with benzyl alcohol to give the N-Z derivative (14a). (Diagram Presented).
  • 39
    • 1242292793 scopus 로고    scopus 로고
    • note
    • -3.
  • 43
    • 0029912748 scopus 로고    scopus 로고
    • Structure minimizations were performed with a suite of programs: MacroModel version 8.1., Schrödinger, L. L. C. OPLS-AA force field: W. L. Jorgensen, D. S. Maxwell, J. Tirado-Rives, J. Am. Chem. Soc. 1996, 118, 11225-11235.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 11225-11235
    • Jorgensen, W.L.1    Maxwell, D.S.2    Tirado-Rives, J.3
  • 46
    • 1242292797 scopus 로고    scopus 로고
    • note
    • Increased hydrophobicity of the peptides caused greater nonspecific adsorption onto the glass and plastic surfaces of the equipment used for their purification, which lowered the yield.
  • 47
    • 1242270347 scopus 로고    scopus 로고
    • note
    • -1; detection: 215 nm.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.