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Volumn 129, Issue 37, 2007, Pages 11421-11430

Water-soluble phosphinothiols for traceless Staudinger ligation and integration with expressed protein ligation

Author keywords

[No Author keywords available]

Indexed keywords

ORTHOGONAL REACTIVITY; PHOSPHINOTHIOLS; PROTEIN LIGATION; REAGENTS;

EID: 35048850528     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja073204p     Document Type: Article
Times cited : (82)

References (48)
  • 26
    • 35048892167 scopus 로고    scopus 로고
    • Chemical Probes in Biology
    • Schneider, M. P, Ed, Kluwer Academic: Boston, MA
    • Nilsson, B. L.; Soellner, M. B.; Raines, R. T. In Chemical Probes in Biology (NATO ASI Series); Schneider, M. P., Ed.; Kluwer Academic: Boston, MA, 2003; pp 359-369.
    • (2003) NATO ASI Series , pp. 359-369
    • Nilsson, B.L.1    Soellner, M.B.2    Raines, R.T.3
  • 27
    • 33845283266 scopus 로고    scopus 로고
    • We were inspired initially by the common water-soluble disulfide reducing agent, tris(2-carboxyethyl)phosphine (TCEP) (Houk, J.; Whitesides, G. M. J. Am. Chem. Soc. 1987, 109, 6825-6836). Accordingly, we synthesized the water-soluble bis(2-carboxyethyl)thiomethyl phosphine but found its mediation of traceless Staundinger ligations in water to yield a preponderance of amine byproduct (data not shown).
    • We were inspired initially by the common water-soluble disulfide reducing agent, tris(2-carboxyethyl)phosphine (TCEP) (Houk, J.; Whitesides, G. M. J. Am. Chem. Soc. 1987, 109, 6825-6836). Accordingly, we synthesized the water-soluble bis(2-carboxyethyl)thiomethyl phosphine but found its mediation of traceless Staundinger ligations in water to yield a preponderance of amine byproduct (data not shown).
  • 28
    • 35048826866 scopus 로고    scopus 로고
    • Windholz, M., Budavari, S., Blumetti, R. F., Otterbein, E. S., Eds. The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals, 10th ed.; 1983; entry 4611.
    • Windholz, M., Budavari, S., Blumetti, R. F., Otterbein, E. S., Eds. The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals, 10th ed.; 1983; entry 4611.
  • 30
    • 35048867534 scopus 로고    scopus 로고
    • Like the iminophosphorane phosphorus, the thioester carbon becomes more electrophilic and hence susceptible to hydrolysis upon protonation of the iminophosphorane. Thioester hydrolysis would decrease the yield of amide 16 in a pH-dependent manner and is thus consistent with the data in Figure 1.
    • Like the iminophosphorane phosphorus, the thioester carbon becomes more electrophilic and hence susceptible to hydrolysis upon protonation of the iminophosphorane. Thioester hydrolysis would decrease the yield of amide 16 in a pH-dependent manner and is thus consistent with the data in Figure 1.
  • 37
    • 33646465282 scopus 로고    scopus 로고
    • Lee and co-workers have reported that couplings of azide 30 as well as 14 similar azido acids mediated by (diphenylphosphino)methanethiol proceed in quantitative yield (Kim, H.; Cho, J. K.; Aimoto, S.; Lee, Y.-S. Org. Lett. 2006, 8, 1149-1151). These results could not be reproduced in our laboratory.
    • Lee and co-workers have reported that couplings of azide 30 as well as 14 similar azido acids mediated by (diphenylphosphino)methanethiol proceed in "quantitative yield" (Kim, H.; Cho, J. K.; Aimoto, S.; Lee, Y.-S. Org. Lett. 2006, 8, 1149-1151). These results could not be reproduced in our laboratory.
  • 39
    • 0001005285 scopus 로고    scopus 로고
    • Raines, R. T. Chem. Rev. 1998, 98, 1045-1066.
    • (1998) Chem. Rev , vol.98 , pp. 1045-1066
    • Raines, R.T.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.