4530-17-0Relevant articles and documents
On the Double Bond Isostere of the Peptide Bond: Preparation of an Enkephalin Analogue
Hann, Michael M.,Sammes, Peter G.,Kennewell, Peter D.,Taylor, John B.
, p. 307 - 314 (2007/10/02)
Methodology for preparing dipeptide analogues in which a carbon -carbon double bond replaces the normal amide bond is described.Thus, the protected tyrosylglycine analogue, (S)-trans-5-t-butyloxycarbonylamino-6-(4-t-butoxyphenyl)hex-3-enoic acid has been synthesised and incorporated into the Leu-enkephalin analogue (3) by condensation with glycylphenylalanyl-leucine.The enkephalin analogue retained biological activity.The significance of this isosteric replacement of the amide group is discussed.