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

Resins for the Fmoc-/tBu-Synthesis

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)

Materials
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References

1.
Wang S. 1973. p-Alkoxybenzyl Alcohol Resin andp-Alkoxybenzyloxycarbonylhydrazide Resin for Solid Phase Synthesis of Protected Peptide Fragments. J. Am. Chem. Soc.. 95(4):1328-1333. http://dx.doi.org/10.1021/ja00785a602
2.
Fields CG, Fields GB. Solvents for Solid-Phase Peptide Synthesis.29-40. http://dx.doi.org/10.1385/0-89603-273-6:29
3.
Chang C, Meienhofer J. SOLID-PHASE PEPTIDE SYNTHESIS USING MILD BASE CLEAVAGE OF N?FLUORENYLMETHYLOXYCARBONYLAMINO ACIDS, EXEMPLIFIED BY A SYNTHESIS OF DIHYDROSOMATOSTATIN. 11(3):246-249. http://dx.doi.org/10.1111/j.1399-3011.1978.tb02845.x
4.
Sieber P. 1987. An improved method for anchoring of 9-fluorenylmethoxycarbonyl-amino acids to 4-alkoxybenzyl alcohol resins.. Tetrahedron Letters. 28(49):6147-6150. http://dx.doi.org/10.1016/s0040-4039(00)61832-4
5.
GRANDAS A, JORBA X, GIRALT E, PEDROSO E. Anchoring of Fmoc-amino acids to hydroxymethyl resins. 33(5):386-390. http://dx.doi.org/10.1111/j.1399-3011.1989.tb00699.x
6.
Blankemeyer-Menge B, Nimtz M, Frank R. 1990. An efficient method for anchoring fmoc-anino acids to hydroxyl-functionalised solid supports. Tetrahedron Letters. 31(12):1701-1704. http://dx.doi.org/10.1016/s0040-4039(00)88858-9
7.
Mitsunobu O. 1981. Synthesis . 1.
8.
Krch?ák V, Cabel D, Weichsel A, Flegelová Z. 1995. Esterification of polymer-supported hydroxyl groups using the Mitsunobu reaction. Lett Pept Sci. 1(6):277-282. http://dx.doi.org/10.1007/bf00119768

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