Hydroxylamine Wang resin

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.

Replaces: 01-64-0454

Color (visual): white to yellow to beige
Appearance of substance (visual): beads
Loading (determined by elemental analysis of nitrogen): 1.5 - 2.5 mmol/g
Swelling Volume (in DMF): lot specific result
The polymer matrix is copoly (styrene - 1% DVB), 100 - 200 mesh.

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