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Volumn 130, Issue 41, 2008, Pages 13518-13519

Tetrazine ligation: Fast bioconjugation based on inverse-electron-demand Diels-Alder reactivity

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; CYCLOOCTENE; CYSTEINE; SOLVENT; TETRAZINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 53849105464     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja8053805     Document Type: Article
Times cited : (1227)

References (36)
  • 9
    • 85123224860 scopus 로고    scopus 로고
    • Recent examples: Duckworth, B. P.; Xu, J. H.; Taton, T. A.; Guo, A.; Distefano, M. D. Bioconjugate Chem. 2006, 17, 967.
    • Recent examples: Duckworth, B. P.; Xu, J. H.; Taton, T. A.; Guo, A.; Distefano, M. D. Bioconjugate Chem. 2006, 17, 967.
  • 28
    • 0000746413 scopus 로고    scopus 로고
    • For Diels-Alder reactions of styrene and 1b in water: Wijnen, J. W.; Zavarise, S.; Engberts, J. B. F. N.; Chartern, M. J. Org. Chem. 1996, 61, 2001.
    • For Diels-Alder reactions of styrene and 1b in water: Wijnen, J. W.; Zavarise, S.; Engberts, J. B. F. N.; Chartern, M. J. Org. Chem. 1996, 61, 2001.
  • 29
    • 53849125226 scopus 로고    scopus 로고
    • -2 M) was allowed to stir in pure water, 20% decomposition of 1b was noted after 2 h.
    • -2 M) was allowed to stir in pure water, 20% decomposition of 1b was noted after 2 h.
  • 30
    • 0037606916 scopus 로고    scopus 로고
    • The product from trans-cyclooctene and 1a aromatizes upon workup. See: Padwa, A.; Rodriguez, A.; Tohidi, M.; Fukunaga, T. J. Am. Chem. Soc. 1983, 105, 933.
    • The product from trans-cyclooctene and 1a aromatizes upon workup. See: Padwa, A.; Rodriguez, A.; Tohidi, M.; Fukunaga, T. J. Am. Chem. Soc. 1983, 105, 933.
  • 33
    • 0028569229 scopus 로고    scopus 로고
    • Acyl transfer to 8 was most effective when aromatic acylating agents were employed. When aliphatic acylating agents were used, undesired reactivity (presumably via ketene formation) competes with the rate of acylation. It is likely that the rate of acyl transfer to 8 is slow because it is a very electron-deficient aniline. Sugars and peptides can be appended to aromatic acylating agents via terephthaloyl linkers, e.g.: (a) Angelastro, M. R.; Baugh, L. E.; Bey, P.; Burkhart, J. P.; Chen, T.-M.; Durham, S. L.; Hare, C. M.; Huber, E. W.; Janusz, M. J.; Koehl, J. R.; Marquart, A. L.; Mehdi, S.; Peet, N. P. J. Med. Chem. 1994, 37, 4538.
    • Acyl transfer to 8 was most effective when aromatic acylating agents were employed. When aliphatic acylating agents were used, undesired reactivity (presumably via ketene formation) competes with the rate of acylation. It is likely that the rate of acyl transfer to 8 is slow because it is a very electron-deficient aniline. Sugars and peptides can be appended to aromatic acylating agents via terephthaloyl linkers, e.g.: (a) Angelastro, M. R.; Baugh, L. E.; Bey, P.; Burkhart, J. P.; Chen, T.-M.; Durham, S. L.; Hare, C. M.; Huber, E. W.; Janusz, M. J.; Koehl, J. R.; Marquart, A. L.; Mehdi, S.; Peet, N. P. J. Med. Chem. 1994, 37, 4538.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.