TY - CHAP
T1 - Protecting groups in peptide synthesis
AU - Conda-Sheridan, Martin
AU - Krishnaiah, Maddeboina
N1 - Funding Information:
This work was funded by the National Institute of Health-NIGMS, the Nebraska Center for Molecular Target Discovery and Development (1P20GM121316-01A1, PI: Robert Lewis, Project Leader, M.C.-S.), and the American Chemical Society, PRF# 57434-DNI7 (M.C.-S.).
Publisher Copyright:
© Springer Science+Business Media, LLC, part of Springer Nature 2020.
PY - 2020
Y1 - 2020
N2 - The protection of amino acid reactive functionalities including the α-amino group, the side chain (amines, carboxylic acids, alcohols, and thiols), or the carboxylic acid terminus is an essential strategy in peptide chemistry. This is mandatory to prevent polymerization of the amino acids and to minimize undesirable side reactions during the synthetic process. Proper protecting group manipulation strategies can maximize the yield of the desired product or allow the construction of complex peptide-based structures. Thus, the compatibility and orthogonality of each protecting group are key to achieve the proper control of molecular structure. Herein, we describe some common protecting groups and their general unmasking methods, in order to mask and expose amine, carboxylic acid, alcohol, and thiol functionalities to achieve the synthesis of peptides and related molecules.
AB - The protection of amino acid reactive functionalities including the α-amino group, the side chain (amines, carboxylic acids, alcohols, and thiols), or the carboxylic acid terminus is an essential strategy in peptide chemistry. This is mandatory to prevent polymerization of the amino acids and to minimize undesirable side reactions during the synthetic process. Proper protecting group manipulation strategies can maximize the yield of the desired product or allow the construction of complex peptide-based structures. Thus, the compatibility and orthogonality of each protecting group are key to achieve the proper control of molecular structure. Herein, we describe some common protecting groups and their general unmasking methods, in order to mask and expose amine, carboxylic acid, alcohol, and thiol functionalities to achieve the synthesis of peptides and related molecules.
KW - Amino acid side chains
KW - Amino acids
KW - Protecting groups
KW - Protection of amines
KW - Solid-phase peptide synthesis
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U2 - 10.1007/978-1-0716-0227-0_7
DO - 10.1007/978-1-0716-0227-0_7
M3 - Chapter
C2 - 31879921
AN - SCOPUS:85077245031
T3 - Methods in Molecular Biology
SP - 111
EP - 128
BT - Methods in Molecular Biology
PB - Humana Press Inc.
ER -