82464-47-9

Upstream product

• 74974-42-8 (S)-cis-5-t-butoxycarbonylamino-6-(4-t-butoxyphenyl)hex-3-enoylglycyl-L-phenylalanyl-L-leucine methyl ester 
• 74974-40-6 (S)-trans-5-t-butoxycarbonylamino-6-(4-t-butoxyphenyl)hex-3-enoic acid 
• 74974-38-2 (S)-trans-2-t-butoxycarbonylamino-1-(4-t-butoxyphenyl)-6-trimethylsilylhex-3-en-5-yne 

Downstream Products

• 82464-46-8 (R)-trans-6-amino-6-(4-hydroxyphenyl)hex-2-enoylglycyl-L-phenylalanyl-L-leucine 
• 82464-45-7 (R)-trans-5-t-butoxycarbonylamino-6-(4-t-butoxyphenyl)hex-2-enoylglycyl-L-phenylalanyl-L-leucine methyl ester 

Relevant academic research and scientific papers

On the Double Bond Isostere of the Peptide Bond: Preparation of an Enkephalin Analogue

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.