4-(4,6-dimethoxy[1,3,5]triazin-2-yl)-4-methyl-morpholinium chloride (DMTMM): A valuable alternative to PyBOP for solid phase peptide synthesis

Synlett

Volumn , Issue 2, 2000, Pages 275-277

  Falchi, Alessandro ^a   Giacomelli, Giampaolo ^a   Porcheddu, Andrea ^a   Taddei, Maurizio ^a  

^a UNIVERSITY OF SASSARI   (Italy)

Author keywords

Coupling reagents; Peptides; Solid phase synthesis; Triazines

Indexed keywords

TRIAZINE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; PEPTIDE ANALYSIS; PEPTIDE SYNTHESIS; REACTION ANALYSIS;

EID: 0033963499     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2000-6490     Document Type: Article

References (22)

1. Bodanszky, M.; Bodanszky, A. The Practice of Peptide Synthesis, Springer-Verlag: Berlin, 1994; 75.
2. Merrifield, B. In Peptides, Synthesis, Structures, and Applications, B. Gutte Ed., Academic Press, San Diego: 1995; 94.
3. a) Lee, H-W.; Kang, T.W.; Cha, K.H.; Kim, E-N.; Choi, N-H.; Kim, J-W.; Hong, C.H. Synth. Commun. 1998, 28, 1339.
4. b) Hipskind, P. A.; Howbert, J.; Cho, S.; Cronin, J. S.; Fort, S. L.; Ginah, F. O.; Hansen, G. J.; Huff, B. E.; Lobb, K. L.; Martinelli, M. J.; Murray, A. R.; Nixon, J. A.; Staszak, M.; Copp, J. D. J. Org. Chem. 1995, 60, 7033.
5. Taylor, E. C.; Dowling, J. E.; J. Org. Chem. 1997, 62, 1599.
6. Nayyar, N. K.; Hutchinson, D. R.; Martinelli, M. J. J. Org. Chem. 1997, 62, 982.
7. e) Kaminski, Z. J. Synthesis 1987, 917.
8. f) Kaminski, Z. J. Tetrahedron Lett. 1985, 26, 2901.
9. Falorni, M.; Porcheddu, A.; Taddei, M. Tetrahedron Lett. 1999, 40, 4395. Masala, S.; Taddei, M. Org. Lett. 1999, I,1355.
10. Falorni, M.; Porcheddu, A.; Taddei, M. Tetrahedron Lett. 1999, 40, 4395. Masala, S.; Taddei, M. Org. Lett. 1999, I,1355.
11. Falorni, M.; Giacomelli, G.; Porcheddu, A.; Taddei, M. J. Org. Chem. 1999, 64, 8962.
12. Kaminski, Z.J.; Paneth, P.; Rudzinski, J. J. Org. Chem. 1998, 63, 4248.
13. Kaiser, E.; Colescott, R.L.; Bosinger, C.D.; Cook, P.I. Anal. Biochem. 1970, 34, 595.
14. The activation time preceding the coupling process has been related to partial racemisation also in the case of phosphonium salts, see: Albericio, F.; Cases, M.; Alsina, J.; Triolo, S.A.; Carpino, L.A.; Kates, S.A. Tetrahedron Lett. 1997, 38, 4853 and references therein.
15. 3: C 43.40, H 6.19, N 20.25. Found C 43.48; H 6.20, N 20.30.:
16. 3: C 43.40, H 6.19, N 20.25. Found C 43.48; H 6.20, N 20.30.:
17. 3: C 43.40, H 6.19, N 20.25. Found C 43.48; H 6.20, N 20.30.:
18. For an analogous behaviour with isobutyl chloroformate see: Shieh, W-C.; Carlson, J.A.; Shore, M.E. Tetrahedron Lett. 1999, 40, 7167.
19. 2O (0.1 % TFA) fron 80/20 to 20/ 80 in 20 min. Detector UV lamp, λ 254 nm, flow 1 mL / min.
20. We followed the protocol described on the Novabiochem Catalogue & Peptide Synthesis Handbook, 1999, Synthesis Notes, S69.
21. The price of PyBOP is 11.9 Euro per mmol, whereas the cost of 2 (purchasing CDMT and NMM and considering a yield of 90%) is 1.5 Euro per mmol. Prices from Aldrich Catalogue 1999-2000, Italian Lira. Preparing CDMT from trichlorotriazine and MeOH the cost is even lower.
22. Vojkovsky, T. Pept. Res. 1995, 8, 236.