Use of onium salt-based coupling reagents in peptide synthesis

Journal of Organic Chemistry

Volumn 63, Issue 26, 1998, Pages 9678-9683

  Albericio, Fernando ^a   Bofill, Josep M ^a   El Faham, Ayman ^b   Kates, Steven A ^c  

^a UNIVERSITY OF BARCELONA   (Spain)

^b UNIVERSITY OF MASSACHUSETTS   (United States)

^c PERKINELMER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALIPHATIC AMINE; BENZOTRIAZOLE DERIVATIVE; CATION; CYANAMIDE; GUANIDINE DERIVATIVE; PEPTIDE; PHOSPHONIUM DERIVATIVE; PYRROLIDINE DERIVATIVE; REAGENT;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DERIVATIZATION; PEPTIDE SYNTHESIS; SOLID STATE;

EID: 0032567305     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980807y     Document Type: Article

References (37)

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19. X-ray analysis has shown that HATU, HBTU, and HAPyU crystallize in the form of the aminium salts; see: (a) Abdelmoty, I.; Albericio, F.; Carpino, L. A.; Foxman, B. M.; Kates, S. A. Lett. Pept. Sci. 1994, 1, 52-67. (b) Henklein, P.; Costisella, B.; Wray, V.; Domke, T.; Carpino, L. A.; El-Faham, A.; Kates, S. A.; Abdelmoty, A.; Foxman, B. M. In Peptides 1996. Proceedings of the 24th European Peptide Symposium; Ramage R., Epton, R., Eds.; Mayflower Worldwide Ltd.: Birmingham, 1997. For those compounds for which X-ray data have not yet been obtained, generic structural representations are shown. For these reagents, traditional nomenclature has arbitrarily been retained.
20. X-ray analysis has shown that HATU, HBTU, and HAPyU crystallize in the form of the aminium salts; see: (a) Abdelmoty, I.; Albericio, F.; Carpino, L. A.; Foxman, B. M.; Kates, S. A. Lett. Pept. Sci. 1994, 1, 52-67. (b) Henklein, P.; Costisella, B.; Wray, V.; Domke, T.; Carpino, L. A.; El-Faham, A.; Kates, S. A.; Abdelmoty, A.; Foxman, B. M. In Peptides 1996. Proceedings of the 24th European Peptide Symposium; Ramage R., Epton, R., Eds.; Mayflower Worldwide Ltd.: Birmingham, 1997. For those compounds for which X-ray data have not yet been obtained, generic structural representations are shown. For these reagents, traditional nomenclature has arbitrarily been retained.
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36. For an elegant example of the combination of both theoretical and experimental methods in the development of chemical methods for the synthesis of oligodeoxyribonucleotides, see: Wada, T.; Sato, Y.; Honda, F.; Kawahara, S.; Sekine, M. J. Am. Chem. Soc. 1997, 119, 12710-12721.
37. Mixtures containing HOAc for washing instrument lines should be avoided, since HOAc can react with the various coupling reagents, generating extra peaks in the HPLC chromatograms.