TY - JOUR
T1 - Gram-Scale Preparation of C-Terminal-Modified Enkephalin Analogues by Typical Liquid-Phase Peptide Synthesis
AU - Lee, Yeon Sun
N1 - Funding Information:
This work was supported by a grant from the Proof of Concept program (UA15‐178) of the University of Arizona.
Publisher Copyright:
© 2019 John Wiley & Sons, Inc.
PY - 2019/12/1
Y1 - 2019/12/1
N2 - This article describes the gram-scale liquid-phase peptide synthesis of C-terminal-modified enkephalin analogues that possess high analgesic efficacy in animals, high potency for mu and delta opioid receptors, and high metabolic stability and potential blood–brain barrier permeability. Despite the long cycle time and tedious purification steps, liquid-phase synthesis is still a preferred method for large-scale peptide synthesis due to its cost effectiveness (i.e., amount of amino acids and reagents required), easy detection, and isolation of impurities compared with solid-phase synthesis. A robust liquid-phase synthesis protocol is described, involving BOP-assisted coupling and Boc deprotection, which has been well established in the laboratory and is a useful synthetic protocol for cost-effective production of peptide drugs.
AB - This article describes the gram-scale liquid-phase peptide synthesis of C-terminal-modified enkephalin analogues that possess high analgesic efficacy in animals, high potency for mu and delta opioid receptors, and high metabolic stability and potential blood–brain barrier permeability. Despite the long cycle time and tedious purification steps, liquid-phase synthesis is still a preferred method for large-scale peptide synthesis due to its cost effectiveness (i.e., amount of amino acids and reagents required), easy detection, and isolation of impurities compared with solid-phase synthesis. A robust liquid-phase synthesis protocol is described, involving BOP-assisted coupling and Boc deprotection, which has been well established in the laboratory and is a useful synthetic protocol for cost-effective production of peptide drugs.
KW - BOP-assisted coupling
KW - Boc chemistry
KW - C-terminal-modified enkephalins
KW - liquid-phase peptide synthesis
KW - opioid receptors
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U2 - 10.1002/cpps.97
DO - 10.1002/cpps.97
M3 - Article
C2 - 31763797
AN - SCOPUS:85075500800
SN - 1934-3655
VL - 98
JO - Current Protocols in Protein Science
JF - Current Protocols in Protein Science
IS - 1
M1 - e97
ER -