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 hydr
Solid supported synthesis of hydroxamic acids
β Scribed by Adam Golebiowski; Sean Klopfenstein
- Publisher
- Elsevier Science
- Year
- 1998
- Tongue
- French
- Weight
- 185 KB
- Volume
- 39
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
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 group deprotection with trifluoroacetic acid.
π SIMILAR VOLUMES
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.
## Abstrrrct: lk nitroacetyl (S)-proline esfers (Z,3,.5} are reduced by zinc-NH,Cl to the hydroxylamine stage and cyclized toprovide the novel chit-al bicyclic hydroxamic acids (2,4,6). Michael addition of ally1 acrylate on nhmacetic acid derivatives followed by Pd(0) catalyzed intramolecular ally1