Monitoring and quantification on solid support of a by-product formation during peptide synthesis by Tof-SIMS

Tetrahedron Letters

Volumn 40, Issue 34, 1999, Pages 6217-6220

  Enjalbal, C ^a   Maux, D ^a   Subra, G ^a   Martinez, J ^a   Combarieu, R ^b   Aubagnac, J L ^a  

^a UNIVERSITÉ DE MONTPELLIER   (France)

^b PSL RESEARCH UNIVERSITY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

GLUTAMIC ACID;

ARTICLE; CHEMICAL STRUCTURE; COVALENT BOND; CYCLIZATION; MASS SPECTROMETRY; PEPTIDE SYNTHESIS;

EID: 0033588194     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01158-2     Document Type: Article

References (18)

1. Bodanszky, M.; Martinez, J. In The Peptide: Analysis, Synthesis, Biology; Gross, E.; Meienhofer, J., Eds.; Academic Press: New York, 1983; Vol. 5, pp. 111-216.
2. Barber, M.; Bordoli, R. S.; Sedgwick, R. D.; Tyler, A. N. J. Chem. Soc., Chem. Commun. 1981,293,325-327.
3. Fenn, J. B.; Mann, M.; Meng, C. K.; Wong, S. F.; Whitehouse, C. M. Mass Spectrom. Rev. 1990, 9, 37-70.
4. Mann, M.; Hojrup, P.; Roepstorff, P. Biol. Mass Spectrom. 1993, 22, 338-345.
5. Fruchtel, J. S.; Jung, G. Angew. Chem., Int. Ed. Engl. 1996,35,17-42.
6. Dhalluin, C.; Boutillon, C.; Tartar, A.; Lippens, G. J. Am. Chem. Soc. 1997, 119, 10494-10500.
7. (a) Li, W.; Yan, B. Tetrahedron Lett. 1997, 38, 6485-6488.
8. (b) Yan, B. Acc. Chem. Res. 1998, 31, 621-630.
9. (a) Fitzgerald, M. C.; Harris, K. H.; Shevlin, C. G.; Siuzdak, G. Bioorg. Med. Chem. Lett. 1996, 6, 979-982.
10. (b) Carrasco, M. R.; Fitzgerald, M.; Oda, Y.; Kent, S. B. H. Tetrahedron Lett. 1997, 38, 6331-6334.
11. Benninghoven, A.; Rüdenauer, F. G.; Werner, M. W. Secondary Ion Mass Spectrometry, Basic Concepts, Instrumental Aspects, Applications and Trends; John Wiley: New York, 1987.
12. Drouot, C.; Enjalbal, C.; Fulcrand, P.; Martinez, J.; Aubagnac, J.-L.; Combarieu, R.; De Puydt, Y. Rapid Commun. Mass Spectrom. 1996,10,1509-1511.
13. Drouot, C.; Enjalbal, C.; Fulcrand, P.; Martinez, J.; Aubagnac, J.-L.; Combarieu, R.; De Puydt, Y. Tetrahedron Lett. 1997, 38, 2455-2458.
14. Aubagnac, J.-L.; Enjalbal, C.; Subra, G.; Bray, A. M.; Combarieu, R.; Martinez, J. J. Mass Spectrom. 1998, 33, 1094-1103.
15. Enjalbal, C.; Martinez, J.; Subra, G.; Combarieu, R.; Aubagnac, J.-L. Rapid Commun. Mass Spectrom. 1998, 12, 1715-1720.
16. Aubagnac, J.-L.; Enjalbal, C.; Drouot, C.; Combarieu, R.; Martinez, J. J. Mass Spectrom., in press.
17. 2 and DMF, the Fmoc protection was removed by two treatments (3 min and 15 min) with a piperidine solution in DMF (20%, v/v). Fmoc-Ala-OH, Fmoc-Phe-OH and a mixture of Fmoc-Glu(O'Bu)-OH with Pyr-OH (quantity adjusted according to the percentage of desired by-product) were successively coupled.
18. 10