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Synthesis of Enkephalin Analogues

Mohammed Javed, Graham Patrick


School of Engineering and Science, University of the west of Scotland, Paisley, PA1 2BE

Introduction Aims Proposed Synthesis Expected Results


•Enkephalins are endogenous peptides, The aim is to synthesize an enkephalin •The synthesis of GlycylGlycine is
•Synthesis takes advantage of protecting groups and
that act as neurotransmitters in the brain. analogue. This involves the following 4 currently being undertaken in the
coupling groups.
steps:- laboratory. A previous method for
Enkephalins the synthesis has been tried,
1 – Synthesis of GlycylGlycine •Protecting groups are essential for the synthesis.
however, it gave an insufficient
They must be added and removed, in order, to allow
yield.
coupling to take place.
2– Addition of protecting group and •It is likely that the entire synthesis
methyl ester will not be completed in the time
Tyr Gly Gly X Leu allocated, therefore, it is crucial to
synthesize as many key
•Enkephalins bind to the delta receptor
3 – Link Tyrosine to GlycylGlycine PG N Tyr Gly Gly X Leu OMe intermediates as possible, on the
(δ).
and have tyrosine protected by BOC. path towards the synthesis.
•The first enkephalins to be discovered Literature cited
PG N Tyr Gly Gly OH H2N X Leu OMe
were Met-enkephalin and Leu-
enkephalin( structure shown below). 4 – Addition of Dipeptide 1. Patrick, Graham L. (2005). An
introduction to Medicinal
PG N Tyr Gly Gly OMe PG NH X Leu OMe chemistry. OUP. pp.636-637
Structure Activity Relationships 2. Corwin Hansch, P.G. Sammes,
PG N Tyr OH HN Gly Gly OMe PG NH X OH HN Leu OMe T.B. Taylor. “Comprehensive
•Tyrosine is essential for activity
medicinal chemistry, the rational
(phenol ring and nitrogen).
design, mechanistic study and
Tyr Gly Gly X Leu
therapeutic application of
chemical compounds”. Volume 3:
Membranes and receptors, pages
•The ‘X’ represents the amino acid which will be 815-843
altered in the synthesis, which in this case, will be
Phenylalanine.
Acknowledgments

• This is a converging synthesis I would like to express my sincere


thanks to my supervisor Dr graham
Patrick for his time and advice
•This is where several “pieces” (key intermediates) of throughout the present work.
•Phenol ring of Tyrosine is thought to the final product are synthesized separately, then
•Enkephalins are inactivated by For further information
be equivalent to phenol ring of linked together, often near the end of the synthesis.
peptidase enzymes in vivo (orally Please contact mjaved3@fastmail.fm
morphine.
if you have any further queries. A
active) – hydrolyzed between •Tyrosine nitrogen is thought to be link to an online PDF-version of the
Tyrosine and Glycine. equivalent to morphine amine. poster is also available at
H Tyr Gly Gly Phe Leu OH
•Aromatic ring of Phe important
( additional interaction)

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