Summary
Summary Retrosynthesis
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Drug design and mechanisms of drug action - 1st semester Includes bullet points, key diagrams and images
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PeptidesFavourable Properties
High target affinity and selectivity
Potentially fewer off targets
Metabolism doesn’t make toxic products
Don’t accumulate in tissue
Drawbacks of Peptides
Poor oral bioavailability
Poor membrane permeability
Susceptible to enzymes and hydrolysis
Can cause immune response
Expensive to make
Peptide Therapeutics
Endogenous peptide hormones- short acting hormones that bind to intracellular
receptors
Protein-protein interactions
Substrate mimics- enzyme inhibitors
Peptide Synthesis
Condensation reactions are complicated due to side chain reactivity
Normally must protect side chain groups before condensation reactions
Protect using esters, carbamates and ethers which hydrolyse in acidic conditions
Selectivity Issues
Need to control which end of amino acids react with each other
Use protecting groups on either terminal
Amine protection is Fmoc carbamate cleaved by base
Carboxylic protection is t-butyl cleaved by acid
Making Peptides By Solid-phase
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