On-Resin Peptide Cyclization Using the 3-Amino-4-(Methylamino)Benzoic Acid MeDbz Linker

Research output: Chapter in Book/Report/Conference proceeding › Book chapter › Research › peer-review

Standard

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. p. 101-115 (Methods in Molecular Biology, Vol. 2371).

Research output: Chapter in Book/Report/Conference proceeding › Book chapter › Research › peer-review

Harvard

Gless, BH & Olsen, CA 2022, On-Resin Peptide Cyclization Using the 3-Amino-4-(Methylamino)Benzoic Acid MeDbz Linker. in Methods in Molecular Biology. Humana Press, Methods in Molecular Biology, vol. 2371, pp. 101-115. https://doi.org/10.1007/978-1-0716-1689-5_6

APA

Gless, B. H., & Olsen, C. A. (2022). On-Resin Peptide Cyclization Using the 3-Amino-4-(Methylamino)Benzoic Acid MeDbz Linker. In Methods in Molecular Biology (pp. 101-115). Humana Press. Methods in Molecular Biology Vol. 2371 https://doi.org/10.1007/978-1-0716-1689-5_6

Vancouver

Gless BH, Olsen CA. On-Resin Peptide Cyclization Using the 3-Amino-4-(Methylamino)Benzoic Acid MeDbz Linker. In Methods in Molecular Biology. Humana Press. 2022. p. 101-115. (Methods in Molecular Biology, Vol. 2371). https://doi.org/10.1007/978-1-0716-1689-5_6

Author

Gless, Bengt H. ; Olsen, Christian A. / On-Resin Peptide Cyclization Using the 3-Amino-4-(Methylamino)Benzoic Acid MeDbz Linker. Methods in Molecular Biology. Humana Press, 2022. pp. 101-115 (Methods in Molecular Biology, Vol. 2371).

Bibtex

@inbook{1a753929f48749b08f0cc562981fec2e,
title = "On-Resin Peptide Cyclization Using the 3-Amino-4-(Methylamino)Benzoic Acid MeDbz Linker",
abstract = "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.",
keywords = "Cyclic peptide, Cysteine modification, Desulfurization, Macrocyclization, Native chemical ligation (NCL), One-pot procedure, Peptide cyclization, Solid-phase peptide synthesis (SPPS), Thiodepsipeptide",
author = "Gless, {Bengt H.} and Olsen, {Christian A.}",
note = "Funding Information: This work was supported by a LEO Foundation Open Competition Grant (LF-OC-19-000039). Publisher Copyright: {\textcopyright} 2022, Springer Science+Business Media, LLC, part of Springer Nature.",
year = "2022",
doi = "10.1007/978-1-0716-1689-5_6",
language = "English",
isbn = "978-1-0716-1688-8",
series = "Methods in Molecular Biology",
publisher = "Humana Press",
pages = "101--115",
booktitle = "Methods in Molecular Biology",
address = "United States",

}

RIS

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