Letters in Peptide Science

, Volume 6, Issue 2–3, pp 157–163 | Cite as

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

  • 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
Article

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.

Key words

hydroxamic acid linker multiple synthesis solid phase organic chemistry 

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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Copyright information

© Kluwer Academic Publishers 1999

Authors and Affiliations

  • Nicholas J. Ede
    • 1
  • Ian W. James
    • 1
  • Beata M. Krywult
    • 1
  • Rachael M. Griffiths
    • 1
  • Susan N. Eagle
    • 1
  • Ben Gubbins
    • 1
  • Jeffrey A. Leitch
    • 1
  • Wayne R. Sampson
    • 1
  • Andrew M. Bray
    • 1
  1. 1.Chiron Technologies Pty. Ltd.ClaytonAustralia

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