Chemoselective coupling of peptide fragments using the Staudinger ligation

Tetrahedron Letters

Volumn 44, Issue 24, 2003, Pages 4515-4518

  Merkx, Remco ^a   Rijkers, Dirk T S ^a   Kemmink, Johan ^a   Liskamp, Rob M J ^a  

^a UTRECHT UNIVERSITY   (Netherlands)

Author keywords

Amide forming ligation; Azido peptides; Peptide o (diphenylphosphine)phenyl esters; Staudinger ligation

Indexed keywords

PENTAPEPTIDE; PEPTIDE FRAGMENT; TETRAPEPTIDE;

AMINO ACID COMPOSITION; AMINO TERMINAL SEQUENCE; ARTICLE; CARBOXY TERMINAL SEQUENCE; CHEMOSENSITIVITY; MASS SPECTROMETRY; REACTION OPTIMIZATION; STAUDINGER REACTION;

EID: 0037727932     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01014-1     Document Type: Article

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24. The phosphines 1, 2 were synthesized via a carbodiimide-mediated esterification of the peptide acid with o-(diphenylphosphine)phenol. The latter compound was synthesized according to: (a) Herd, O.; Hessler, A.; Hingst, M.; Machnitzki, P.; Tepper, M.; Stelzer, O. Catal. Today 1998, 42, 413-420; (b) Herd, O.; Hessler, A.; Hingst, M.; Tepper, M.; Stelzer, O. J. Organomet. Chem. 1998, 552, 69-76.
25. The phosphines 1, 2 were synthesized via a carbodiimide-mediated esterification of the peptide acid with o-(diphenylphosphine)phenol. The latter compound was synthesized according to: (a) Herd, O.; Hessler, A.; Hingst, M.; Machnitzki, P.; Tepper, M.; Stelzer, O. Catal. Today 1998, 42, 413-420; (b) Herd, O.; Hessler, A.; Hingst, M.; Tepper, M.; Stelzer, O. J. Organomet. Chem. 1998, 552, 69-76.
26. Compound 3 was synthesized by diazotransfer as described in the literature: (a) Alper, P. B.; Hung, S.-C.; Wong, C.-H. Tetrahedron Lett. 1996, 37, 6029-6032; (b) Lundquist, J. T., IV; Pelletier, J. C. Org. Lett. 2001, 3, 781-783.
27. Compound 3 was synthesized by diazotransfer as described in the literature: (a) Alper, P. B.; Hung, S.-C.; Wong, C.-H. Tetrahedron Lett. 1996, 37, 6029-6032; (b) Lundquist, J. T., IV; Pelletier, J. C. Org. Lett. 2001, 3, 781-783.
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30. 2O 9/1 v/v at pH 3.72 at 278.1 K on a Varian INOVA-500 NMR spectrometer using a TOCSY pulse-sequence. Based on amide NH integration signals the NH-Leu-αCH ligation product was estimated to be present in 23-33% of the isolated peptides.
31. 5a.
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