Condensation reagent especially suited for coupling of sterically hindered amino acids. Superior suppression of racemization.
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Available in bulk.
Mechanism of reaction:
- PPAA activates carboxylic acid and facilitates the reaction with nucleophiles
- Water formed during the reaction is being removed
Compatible Bases R'3N: Triethylamine, DIPEA, N-Ethyl-morpholine
References:
Amid bond formation:
H.Wissmann, H.-J.Kleiner, Angew .Chem. Int. Ed. 1980; 19: 133-134.
R. Escher, P. Büning, Angew. Chem. Int. Ed. 1986, 108: 277-278.
H.D.Rich, P.Raman, Y.Angell; WO 98/46247, 1998.
H.G.Bossler, D.Seebach, Helv. Chim. Acta 1994; 77: 1124.
Comparison of epimerisation:
J. Hiebl, D.P.Alberts., J. Pept. Res. 1999; 54: 54-65.
J.R. Dunetz, Y. Xiang, A. Baldwin, J. Ringling, Org. Lett. 2011; 13(19): 5048-5051.
Peptides with sterical hindrance:
M. Feigel, J. Am. Chem. Soc. 1986; 108: 181.
Other condensation reactions:
M.Wedel, A.Walter, F.-P. Montforts, Eur. J. Org. Chem. 2001; 1681-1687.
B.Napierski, H.-P.Rebenstock, W.Holla; US 6,407,258B1, 2002. S.Hermann, DE 100 63 493 A1, 2002.
F.Burkhart, M.Hoffmann, H. Kessler, Angew. Chem. Int. Ed. 1997; 36: 1191-1192.