8.55117
Hydroxylamine Wang resin
Novabiochem®
Synonym(s):
Amino-oxy Wang resin
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About This Item
NACRES:
NA.22
UNSPSC Code:
12352116
Quality Level
product line
Novabiochem®
form
beads
reaction suitability
reaction type: Fmoc solid-phase peptide synthesis
manufacturer/tradename
Novabiochem®
application(s)
peptide synthesis
storage temp.
2-8°C
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.
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.
Analysis Note
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.
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.
Other Notes
Replaces: 01-64-0454
Legal Information
Novabiochem is a registered trademark of Merck KGaA, Darmstadt, Germany
Storage Class
11 - Combustible Solids
wgk
WGK 1
flash_point_f
Not applicable
flash_point_c
Not applicable
Certificates of Analysis (COA)
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