The 1,1-dioxobenzo[b]thiophene-2-ylmethyloxycarbonyl (Bsmoc) amino- protecting group

Journal of Organic Chemistry

Volumn 64, Issue 12, 1999, Pages 4324-4338

  Carpino, Louis A ^a   Ismail, Mohamed ^a   Truran, George A ^a   Mansour, E M E ^a,b   Iguchi, Shin ^a   Ionescu, Dumitru ^a,c   El Faham, Ayman ^a,b   Riemer, Christoph ^a   Warrass, Ralf ^a  

^a UNIVERSITY OF MASSACHUSETTS   (United States)

^b Alexandria University Faculty Of Science   (Egypt)

^c UNIVERSITY OF BUCHAREST   (Romania)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYL DERIVATIVE;

AMINO ACID SEQUENCE; AQUEOUS SOLUTION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; PEPTIDE SYNTHESIS; PHASE SEPARATION; SYNTHESIS;

EID: 0033546356     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo982140l     Document Type: Article

References (43)

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3. Carpino, L. A.; Philbin, M. J. Org. Chem. 1999, 64, 4315.
4. Reference 1, Supporting Information.
5. In view of the presence of a strong styrene chromophore in the Bsmoc residue, one would expect that methods similar to those used for the Fmoc group to follow resin loading, the coupling and deblocking steps, etc., could be used in this case as well. For the Fmoc methods, see Meienhofer, J.; Waki, M.; Heimer, E. P.; Lambras, T. L.; Makofske, R. C.; Chang, C.-D. Int. J. Pept. Protein Res. 1979, 13, 35.
6. Marfey, P. Carlsberg Res. Commun. 1984, 49, 591.
7. Granitza, D.; Beyermann, M.; Wensehuh, H.; Haber, H.; Carpino, L. A.; Truran, G. A., Bienert, M. J. Chem. Soc., Chem. Commun. 1995, 2223. It is not certain whether this technique is feasible in the case of Bsmoc amino acids, some of which, e.g., that of glycine, are sensitive to DMAP.
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14. (a) For a brief review of the use of the acyl carrier protein decapeptide (65-74) as a test sequence for solid phase assembly, see: Adams, J. H.; Cook, R. M.; Hudson, D.; Jammalamaddaka, V.; Lyttle, M. H.; Songster, M. F. J. Org. Chem. 1998, 63, 3706, footnote 21.
15. (b) Reference 10b.
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19. For recent alternative approaches to minimize β-catalyzed aspartimide formation during Fmoc assembly and references to earlier work, see: (a) Karlström, A.; Undén, A. Int. J. Pept. Protein Res. 1996, 48, 305. (b) Zhang, H.; Wang, Y.; Voelter, W. Chem. Lett. 1995, 1111. (c) Yang, Y.; Sweeney, W. V.; Schneider, K.; Thörquist, S.; Chait, B. T.; Tam, J. P. Tetrahedron Lett. 1994, 35, 9689. (d) Dölling, R.; Beyermann, M.; Haenel, J.; Kernchen, F.; Krause, E.; Franke, P.; Brudel, M.; Bienert, M. J. Chem. Soc., Chem. Commun. 1994, 853 and ref 13.
20. For recent alternative approaches to minimize β-catalyzed aspartimide formation during Fmoc assembly and references to earlier work, see: (a) Karlström, A.; Undén, A. Int. J. Pept. Protein Res. 1996, 48, 305. (b) Zhang, H.; Wang, Y.; Voelter, W. Chem. Lett. 1995, 1111. (c) Yang, Y.; Sweeney, W. V.; Schneider, K.; Thörquist, S.; Chait, B. T.; Tam, J. P. Tetrahedron Lett. 1994, 35, 9689. (d) Dölling, R.; Beyermann, M.; Haenel, J.; Kernchen, F.; Krause, E.; Franke, P.; Brudel, M.; Bienert, M. J. Chem. Soc., Chem. Commun. 1994, 853 and ref 13.
21. For recent alternative approaches to minimize β-catalyzed aspartimide formation during Fmoc assembly and references to earlier work, see: (a) Karlström, A.; Undén, A. Int. J. Pept. Protein Res. 1996, 48, 305. (b) Zhang, H.; Wang, Y.; Voelter, W. Chem. Lett. 1995, 1111. (c) Yang, Y.; Sweeney, W. V.; Schneider, K.; Thörquist, S.; Chait, B. T.; Tam, J. P. Tetrahedron Lett. 1994, 35, 9689. (d) Dölling, R.; Beyermann, M.; Haenel, J.; Kernchen, F.; Krause, E.; Franke, P.; Brudel, M.; Bienert, M. J. Chem. Soc., Chem. Commun. 1994, 853 and ref 13.
22. For recent alternative approaches to minimize β-catalyzed aspartimide formation during Fmoc assembly and references to earlier work, see: (a) Karlström, A.; Undén, A. Int. J. Pept. Protein Res. 1996, 48, 305. (b) Zhang, H.; Wang, Y.; Voelter, W. Chem. Lett. 1995, 1111. (c) Yang, Y.; Sweeney, W. V.; Schneider, K.; Thörquist, S.; Chait, B. T.; Tam, J. P. Tetrahedron Lett. 1994, 35, 9689. (d) Dölling, R.; Beyermann, M.; Haenel, J.; Kernchen, F.; Krause, E.; Franke, P.; Brudel, M.; Bienert, M. J. Chem. Soc., Chem. Commun. 1994, 853 and ref 13.
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24. On the other hand, Bsmoc-Gln(Trt)-OH has previously been used successfully in rapid solution syntheses (see refs 1 and 2 and the synthesis of heptapeptide 23 described herein), possibly because earlier syntheses have involved a greater excess of TAEA than needed or used in current work. The presence of excess TAEA modifies the solvent properties of the aqueous phase during the extraction process but may also serve to remove some of the desired growing peptide as well as the byproducts. It should be noted that structures 14-16 are assigned on the basis of analogy to the corresponding products derived from piperidine. None of these materials has been isolated and characterized unequivocally.
25. a values, taken from Perrin, D. D. The Dissociation Constants of Organic Bases; Butterworths: London, 1965, are piperidine (11.12), piperazine (9.81, 5.55), morpholine (8.33), and ethanolamine (9.51).
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29. Compare: (a) Carpino, L. A.; Sadat-Aalaee, D.; Chao, H.-G.; DeSelms, R. H. J. Am. Chem. Soc. 1990, 112, 9651. (b) Carpino, L. A.; Mansour, E. M. E.; Sadat-Aalaee, D. J. Org. Chem. 1991, 56, 2611.
30. Compare: (a) Carpino, L. A.; Sadat-Aalaee, D.; Chao, H.-G.; DeSelms, R. H. J. Am. Chem. Soc. 1990, 112, 9651. (b) Carpino, L. A.; Mansour, E. M. E.; Sadat-Aalaee, D. J. Org. Chem. 1991, 56, 2611.
31. 1,4
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