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Resins for the Fmoc-/tBu-Synthesis of Peptide Acids

Chemfiles Volume 3 Article 4

The TFA-labile Wang resin is a standard support for batch synthesis of peptide acids following the Fmoc-/tBu-protection scheme.(1,2) It is easily cleaved by treatment with 95% TFA. Special attention should be given to the attachment of the first amino acid residue to this benzyl alcohol type support, because the activation step can lead to a substantial degree of racemization. For the incorporation of the C-terminal amino acids, the following coupling methods are recommended: carbodiimide/dimethyl aminopyridine (DMAP) in dichloromethane,(3) 2,6-dichlorobenzoyl chloride/pyridine in dimethyl formamide (DMF),(4) 1- hydroxybenzotriazole (HOBt)/N,N´-dicyclohexylcarbodiimide (DCC) in DMF (catalytic amounts of DMAP optional),(5) 1-(2- mesitylenesulfonyl)-3-nitro-1H-1,2,4-triazole (MSNT) in the presence of N-methylimidazole,(6) or the Mitsunobu coupling reaction.(7,8)

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  1. Wang, S. S. J. Am. Chem. Soc. 1973, 95, 1328.
  2. Guy, C. A.; Fields, G. B. Methods Enzymol., Vol. 289 (Solid-Phase Peptide Synthesis); G. B. Fields, ed., Academic Press; San Diego, 1997; p. 29.
  3. Chang, C. D.; Meienhofer, J. Int. J. Pep. Protein Res. 1978, 11, 246.
  4. Sieber, P. Tetrahedron Lett. 1987 28, 6147.
  5. Grandas, A. et al. Int. J. Pep. Protein Res. 1989, 33, 386.
  6. Blankemeyer-Menge, B. et al. Tetrahedron Lett. 1990 31, 1701.
  7. Mitsunobu, O. Synthesis 1981, 1.
  8. Krchnák, V. et al. Lett Pept. Sci. 1994, 1, 277.

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