Solid Phase Peptide Synthesis

Post date: Jul 5, 2017 6:29:59 AM

Bruce Merrifield was awarded the 1984 Nobel Prize in Chemistry for his work on Solid Phase Peptide Synthesis (SPPS)

Nice intro to the field and Merrifield's pioneering contribution: http://centennial.rucares.org/index.php?page=Synthesizing_Proteins

Example of modern day advances in SPPS from Danishefsky group: http://www.pnas.org/content/110/29/11708.full

Example of protecting group often used in SPPS: the FMOC group http://pubs.rsc.org/en/content/articlelanding/2015/ra/c5ra23441g#!divAbstract The authors write in the abstract: "Here, we report an efficient Fmoc-deprotection solution containing piperazine and DBU which can cause complete removal of the Fmoc group in less than a minute. This combination rivals piperidine in speediness as revealed by kinetic studies." Pretty amazing that a protecting group can be removed under such mild conditions and so fast! The aromaticity of the fluorene anion is the key here (pKa = 23, as opposed to 33 for diphenylmethane)

Example of a modern-day SPPS instrument: CEM Liberty automated Microwave Multiple CHS Peptide Synthesizer http://cem.com/liberty-blue/ The Peptide Synthesis Core Facility at UCLA has one