On-Resin Peptide Cyclization Using the 3-Amino-4-(Methylamino)Benzoic Acid MeDbz Linker
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On-Resin Peptide Cyclization Using the 3-Amino-4-(Methylamino)Benzoic Acid MeDbz Linker. / Gless, Bengt H.; Olsen, Christian A.
Methods in Molecular Biology. Humana Press, 2022. s. 101-115 (Methods in Molecular Biology, Bind 2371).Publikation: Bidrag til bog/antologi/rapport › Bidrag til bog/antologi › Forskning › fagfællebedømt
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TY - CHAP
T1 - On-Resin Peptide Cyclization Using the 3-Amino-4-(Methylamino)Benzoic Acid MeDbz Linker
AU - Gless, Bengt H.
AU - Olsen, Christian A.
N1 - Funding Information: This work was supported by a LEO Foundation Open Competition Grant (LF-OC-19-000039). Publisher Copyright: © 2022, Springer Science+Business Media, LLC, part of Springer Nature.
PY - 2022
Y1 - 2022
N2 - Cyclic peptides are becoming increasingly important in drug discovery due to their specific binding properties, larger surface area compared to small molecules, and their ready and modular synthetic accessibility. In this protocol, we describe an on-resin, cleavage-inducing cyclization methodology for the synthesis of cyclic thiodepsipeptides and cyclic homodetic peptides using the 3-amino-4-(methylamino)benzoic acid (MeDbz) linker. We further describe three post-cyclization one-pot procedures, which include desulfurization, disulfide bond formation, and S-alkylation of cysteine residues.
AB - Cyclic peptides are becoming increasingly important in drug discovery due to their specific binding properties, larger surface area compared to small molecules, and their ready and modular synthetic accessibility. In this protocol, we describe an on-resin, cleavage-inducing cyclization methodology for the synthesis of cyclic thiodepsipeptides and cyclic homodetic peptides using the 3-amino-4-(methylamino)benzoic acid (MeDbz) linker. We further describe three post-cyclization one-pot procedures, which include desulfurization, disulfide bond formation, and S-alkylation of cysteine residues.
KW - Cyclic peptide
KW - Cysteine modification
KW - Desulfurization
KW - Macrocyclization
KW - Native chemical ligation (NCL)
KW - One-pot procedure
KW - Peptide cyclization
KW - Solid-phase peptide synthesis (SPPS)
KW - Thiodepsipeptide
U2 - 10.1007/978-1-0716-1689-5_6
DO - 10.1007/978-1-0716-1689-5_6
M3 - Book chapter
C2 - 34596845
AN - SCOPUS:85116868746
SN - 978-1-0716-1688-8
T3 - Methods in Molecular Biology
SP - 101
EP - 115
BT - Methods in Molecular Biology
PB - Humana Press
ER -
ID: 289306847