Hydroxylamine Wang resin

Description

• General description: An excellent support for the preparation of peptide hydroxamic acids [1] by Fmoc SPPS. Acylation of the resin has been carried out using TBTU/DIPEA activation [1]. Alkylation of the resin-bound nitrogen has been effected using TMOF/DCE/AcOH for imine formation, followed by reduction with BH3-pyridine [2], by base-mediated alkylation of the N-Boc-protected hydroxylamine, followed by Boc removal with 20% TFA in DCM [3], or by Michael-addition [4]. Cleavage of hydroxamates from the resin has been effected with TFA/DCM/water (70:28:2) [1] or TFA/DCM (1:1) [2]. Hydroxylamine Wang resin has also been utilized to prepare tertiary amines by base-mediated elimination of the quaternized polymer-bound hydroxylamine [3, 5]. Associated Protocols and Technical Articles Protocols for Loading of Peptide Synthesis Resins Literature references[1] C. D. Floyd, et al. (1996) Tetrahedron Lett., 37, 8045.[2] D. E. Robinson & M. W. Holladay (2000) Org. Lett., 2, 2777. [3] P. Blaney, et al. (2000) Tetrahedron Lett., 41, 6635. [4] A. Volonterio, et al. (2002) Eur. J. Org. Chem., 428. [5] P. Blaney, et al. (2000) Tetrahedron Lett., 41, 6639.
• Linkage: Replaces: 01-64-0454
• Analysis Note: Color (visual): white to yellow to beigeAppearance of substance (visual): beadsLoading (determined by elemental analysis of nitrogen): 1.5 - 2.5 mmol/gSwelling Volume (in DMF): lot specific resultThe polymer matrix is copoly (styrene - 1% DVB), 100 - 200 mesh.
• Legal Information: Novabiochem is a registered trademark of Merck KGaA, Darmstadt, Germany