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Synthesis of hydroxamic acids using SynPhase™ crowns: Development of the hydroxylamine trityl linker

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Summary

The synthesis of peptide and small molecule hydroxamic acids utilising SynPhase™ crowns is demonstrated. A hydroxylamine trityl linker is generated from chlorotrityl derivatised Synphase™ crowns by reaction with N-hydroxyphthalimide followed by subsequent deprotection. The loading of hydroxylamine crowns is quantified spectrophotometrically by measuring phthalhydrazide absorbance at 346 nm.

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Abbreviations

AcCl:

acetyl chloride

DCM:

dichloromethane

DIC:

1,3-diisopropylcarbodiimide

DIEA:

diisopropylethylamine

DMF:

dimethylformamide

DMSO:

dimethylsulfoxide

EDT:

1,2-ethanedithiol

ESMS:

electrospray mass spectrometry

Fmoc:

9-fluorenylmethoxycarbonyl

HBTU:

2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate

HOBt:

1-hydroxybenzotriazole

HOPhth:

N-hydroxyphthalimide

HPLC:

high performance liquid chromatography

MeOH:

methanol

NMM:

N-methylmorpholine

NMR:

nuclear magnetic resonance

TFA:

trifluoroacetic acid

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Authors and Affiliations

  1. Chiron Technologies Pty. Ltd., 11 Duerdin Street, 3168, Clayton, VIC, Australia

    Nicholas J. Ede, Ian W. James, Beata M. Krywult, Rachael M. Griffiths, Susan N. Eagle, Ben Gubbins, Jeffrey A. Leitch, Wayne R. Sampson & Andrew M. Bray

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  1. Nicholas J. Ede
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  2. Ian W. James
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  3. Beata M. Krywult
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  4. Rachael M. Griffiths
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  5. Susan N. Eagle
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  6. Ben Gubbins
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  7. Jeffrey A. Leitch
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  8. Wayne R. Sampson
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  9. Andrew M. Bray
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Correspondence to Nicholas J. Ede.

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Ede, N.J., James, I.W., Krywult, B.M. et al. Synthesis of hydroxamic acids using SynPhase™ crowns: Development of the hydroxylamine trityl linker. Lett Pept Sci 6, 157–163 (1999). https://doi.org/10.1007/BF02443631

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  • DOI: https://doi.org/10.1007/BF02443631

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