Enkephalins are endogenous peptides, that act as neurotransmitters in the brain. The aim is to synthesize an analogue. This involves the following 4 steps:1 - Synthesis of GlycylGlycine Proposed Synthesis Synthesis takes advantage of protecting groups and coupling groups.
Enkephalins are endogenous peptides, that act as neurotransmitters in the brain. The aim is to synthesize an analogue. This involves the following 4 steps:1 - Synthesis of GlycylGlycine Proposed Synthesis Synthesis takes advantage of protecting groups and coupling groups.
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Enkephalins are endogenous peptides, that act as neurotransmitters in the brain. The aim is to synthesize an analogue. This involves the following 4 steps:1 - Synthesis of GlycylGlycine Proposed Synthesis Synthesis takes advantage of protecting groups and coupling groups.
Copyright:
Attribution Non-Commercial (BY-NC)
Available Formats
Download as PPT, PDF, TXT or read online from Scribd
•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)
Amino Acids, Peptides and Proteins in Organic Chemistry 1 - Origins and Synthesis of Amino Acids (Amino Acids, Peptides and Proteins in Organic Chemistry (VCH) ) PDF