메뉴 건너뛰기




Volumn 16, Issue 4, 2010, Pages 1124-1127

Postsynthetic modification of peptides: Chemoselective C-arylation of tryptophan residues

Author keywords

Arylation; C h activation; Indoles; Palladium; Peptides

Indexed keywords

ARYL IODIDES; ARYLATIONS; C-H ACTIVATION; CHEMOSELECTIVE; INDOLES; POSTSYNTHETIC MODIFICATION; TRYPTOPHAN RESIDUES;

EID: 76549088533     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200902676     Document Type: Article
Times cited : (150)

References (66)
  • 19
    • 67649488045 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2009, 48, 5094-5115;
    • (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 5094-5115
  • 21
    • 34249936878 scopus 로고    scopus 로고
    • The direct oxidative cross-coupling of two C-H bonds from unactivated arenes recently reported by Fagnou is considerably less developed
    • The direct oxidative cross-coupling of two C-H bonds from unactivated arenes recently reported by Fagnou is considerably less developed. D. R. Stuart, K. Fagnou, Science 2007, 316, 1172-1175.
    • (2007) Science , vol.316 , pp. 1172-1175
    • Stuart, D.R.1    Fagnou, K.2
  • 28
    • 52049102506 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2008, 47, 6452-6455;
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 6452-6455
  • 31
  • 41
    • 70349928947 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2009, 48, 6511-6515;
    • (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 6511-6515
  • 44
    • 59049094555 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2009, 48, 1138-1143.
    • (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 1138-1143
  • 50
    • 39849083252 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2008, 47, 1473-1476.
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 1473-1476
  • 52
    • 0037008930 scopus 로고    scopus 로고
    • For pionering work of hruby in this field, including the synthesis of C2-arylated Trp derivative through a multistep sequence
    • For pionering work of Hruby in this field, including the synthesis of C2-arylated Trp derivative through a multistep sequence, see: W. Wang, M. Cai, C, Xiong, J. Zhang, V. J. Hruby, Tetrahedron 2002, 55,7365-7374.
    • (2002) Tetrahedron , vol.55 , pp. 7365-7374
    • Wang, W.1    Cai, M.2    Xiong, C.3    Zhang, J.4    Hruby, V.J.5
  • 53
    • 76549083417 scopus 로고    scopus 로고
    • Under the original Larrosa conditions (temperature range from 20 to 80°C), the arylation of Trp derivatives does not proceed, starting materials being recovered unchanged
    • Under the original Larrosa conditions (temperature range from 20 to 80°C), the arylation of Trp derivatives does not proceed, starting materials being recovered unchanged.
  • 57
    • 61849182496 scopus 로고    scopus 로고
    • Preliminary results indicate that free amino groups are not tolerated in peptides where Trp is the N-terminal amino acid. Probably, because of the formation of stable Pd complexes that quench the reaction
    • Preliminary results indicate that free amino groups are not tolerated in peptides where Trp is the N-terminal amino acid. Probably, because of the formation of stable Pd complexes that quench the reaction. For instance, see J. Vicente, I. Saura-Llamas, J.-A. GarciaLópez, Organometallics 2009,28, 448-464.
    • (2009) Organometallics , vol.28 , pp. 448-464
    • Vicente, J.1    Saura-Llamas, I.2    Garcialópez, J.-A.3
  • 58
    • 76549099512 scopus 로고    scopus 로고
    • The systematic exploration of racemization-prone petide sequences will be the subject of furher studies in this project
    • The systematic exploration of racemization-prone petide sequences will be the subject of furher studies in this project.
  • 59
    • 76549111844 scopus 로고    scopus 로고
    • The reaction of Cys-containing peptides was not experimentally tested, but clear analogy with Met peptide (3h) indicates that should not be a good substrate for arylation
    • The reaction of Cys-containing peptides was not experimentally tested, but clear analogy with Met peptide (3h) indicates that should not be a good substrate for arylation.
  • 65
    • 70349918273 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2009, 48, 5628-5632.
    • (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 5628-5632


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.