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Piperidine is also commonly used as a base for the deprotection of Fmoc-amino acids used in solid-phase peptide synthesis. Piperidine is listed as a Table II precursor under the United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances due to its use (peaking in the 1970s) in the clandestine manufacture of ...
1-Boc-4-AP (tert-butyl 4-(phenylamino)piperidine-1-carboxylate) is a compound used as an intermediate in the manufacture of fentanyl, as well as various related derivatives such as butyrylfentanyl, furanylfentanyl, benzylfentanyl and homofentanyl, among others.
4-Benzylpiperidine acts as a monoamine releasing agent with 20- to 48-fold selectivity for releasing dopamine versus serotonin. It is most efficacious as a releaser of norepinephrine , with an EC 50 of 109 nM (DA), 41.4 nM (NE), and 5,246 nM ( 5-HT ).
20% piperidine in DMF (Fmoc group has an approximate half life of 6 seconds in this solution) [8] 5% piperazine, 1% DBU and 1% formic acid in DMF. This method avoids the use of strictly controlled piperidine. [9] No side product was observed for a peptide with 9 residues synthesized with this method. [10]
The tert-butyloxycarbonyl protecting group or tert-butoxycarbonyl protecting group [1] (BOC group) is an acid-labile protecting group used in organic synthesis. The BOC group can be added to amines under aqueous conditions using di- tert -butyl dicarbonate in the presence of a base such as sodium hydroxide :
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Fmoc/tBu SPPS is less atom-economical, as the fluorenyl group is much larger than the Boc group. Accordingly, prices for Fmoc amino acids were high until the large-scale piloting of one of the first synthesized peptide drugs, enfuvirtide, began in the 1990s, when market demand adjusted the relative prices of Fmoc- vs Boc- amino acids.
[1] It consists of a piperidine ring with a carboxylic acid moiety in the iso position (and as such is also known as "4-piperidinecarboxylic acid"). References