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Liquid phase peptide synthesis via one‐pot nanostar sieving (PEPSTAR)

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Title: Liquid phase peptide synthesis via one‐pot nanostar sieving (PEPSTAR)
Authors: Yeo, J
Peeva, L
Chung, S
Gaffney, P
Kim, D
Luciani, C
Tsukanov, S
Seibert, K
Kopach, M
Albericio, F
Livingston, A
Item Type: Journal Article
Abstract: Herein, a one‐pot liquid phase peptide synthesis featuring iterative addition of amino acids to a ‘nanostar’ support, with organic solvent nanofiltration (OSN) for isolation of the growing peptide after each synthesis cycle is reported. A cycle consists of coupling, Fmoc removal, then sieving out of the reaction by‐products via nanofiltration in a reactor‐separator, or synthesizer apparatus where no phase or material transfers are required between cycles. The three‐armed and monodisperse nanostar facilitates both efficient nanofiltration and real‐time reaction monitoring of each process cycle. This enabled the synthesis of peptides more efficiently while retaining the full benefits of liquid phase synthesis. PEPSTAR was validated initially with the synthesis of enkephalin‐like model penta‐ and decapeptides, then octreotate amide and finally octreotate. The crude purities compared favorably to vendor produced samples from solid phase synthesis.
Issue Date: 29-Mar-2021
Date of Acceptance: 14-Jan-2021
URI: http://hdl.handle.net/10044/1/86125
DOI: 10.1002/anie.202014445
ISSN: 1433-7851
Publisher: Wiley
Start Page: 7786
End Page: 7795
Journal / Book Title: Angewandte Chemie International Edition
Volume: 60
Issue: 14
Copyright Statement: © 2021 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
Sponsor/Funder: Eli Lilly & Company (USA)
Funder's Grant Number: 4900653675
Keywords: Science & Technology
Physical Sciences
Chemistry, Multidisciplinary
liquid phase peptide synthesis
organic solvent nanofiltration (OSN)
liquid phase peptide synthesis
organic solvent nanofiltration (OSN)
Organic Chemistry
03 Chemical Sciences
Publication Status: Published
Article Number: anie.202014445
Online Publication Date: 2021-01-14
Appears in Collections:Chemical Engineering
Faculty of Natural Sciences
Faculty of Engineering

This item is licensed under a Creative Commons License Creative Commons