A novel approach to the solid supported synthesis of hydroxamic acids was developed. It employs oxime resin and unlike all previously reported methods allows for the use of acid labile protecting groups. Cleavage is induced by treatment with tert-butyldimethylsilyl-O-hydroxylamine, followed by silyl
Solid phase synthesis of peptide hydroxamic acids
β Scribed by Jack J. Chen; Arno F. Spatola
- Publisher
- Elsevier Science
- Year
- 1997
- Tongue
- French
- Weight
- 225 KB
- Volume
- 38
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
The synthesis of peptide hydroxamic acids has been performed on a solid support. A carboxyl group of a peptide synthesized on/xTa-methylbenzhydrylaminΒ’ (pMBHA) resin was converted to a hydroxamate functional group by condensing with NH2OBzl, which was found preferable to NH2OtBu or NH2OTrt. The hydroxama~ benzyl protecting group was removed subsequently during I-IF cleavage of the puptide resin. Five peptide hydroxamie acids wexe prepared according to this new method,
π SIMILAR VOLUMES
Boc/'Z-protected PNA oligomers were synthesised on solid phase. The use of the allylic HYCRON resin allowed for the application of both Boc-and Fmoc-protecting groups. Highest yields were obtained when the monomeric building block was synthesised on solid phase rather than loaded as preformed unit.
A novel linkage for the solid-phase synthesis of hydroxamic acids is described. The linkage is stable to all reagents commonly used in Fmoc peptide synthsis. Cleavage is induced by treatment with trifluoroacetie acid, providing hydroxamic acids in high purity and good yields.