Facile Preparation of PNA-Peptide Conjugates with a Polar Maleimide-Thioether Linkage

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

Standard

Facile Preparation of PNA-Peptide Conjugates with a Polar Maleimide-Thioether Linkage. / Hansen, Anna Mette; Shaikh, Ashif Yasin; Franzyk, Henrik.

Peptide Nucleic Acids: Methods and Protocols. ed. / Peter E. Nielsen. Humana Press, 2020. p. 97-118 (Methods in molecular biology (Clifton, N.J.), Vol. 2105).

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

Harvard

Hansen, AM, Shaikh, AY & Franzyk, H 2020, Facile Preparation of PNA-Peptide Conjugates with a Polar Maleimide-Thioether Linkage. in PEN (ed.), Peptide Nucleic Acids: Methods and Protocols. Humana Press, Methods in molecular biology (Clifton, N.J.), vol. 2105, pp. 97-118. https://doi.org/10.1007/978-1-0716-0243-0_6

APA

Hansen, A. M., Shaikh, A. Y., & Franzyk, H. (2020). Facile Preparation of PNA-Peptide Conjugates with a Polar Maleimide-Thioether Linkage. In P. E. N. (Ed.), Peptide Nucleic Acids: Methods and Protocols (pp. 97-118). Humana Press. Methods in molecular biology (Clifton, N.J.) Vol. 2105 https://doi.org/10.1007/978-1-0716-0243-0_6

Vancouver

Hansen AM, Shaikh AY, Franzyk H. Facile Preparation of PNA-Peptide Conjugates with a Polar Maleimide-Thioether Linkage. In PEN, editor, Peptide Nucleic Acids: Methods and Protocols. Humana Press. 2020. p. 97-118. (Methods in molecular biology (Clifton, N.J.), Vol. 2105). https://doi.org/10.1007/978-1-0716-0243-0_6

Author

Hansen, Anna Mette ; Shaikh, Ashif Yasin ; Franzyk, Henrik. / Facile Preparation of PNA-Peptide Conjugates with a Polar Maleimide-Thioether Linkage. Peptide Nucleic Acids: Methods and Protocols. editor / Peter E. Nielsen. Humana Press, 2020. pp. 97-118 (Methods in molecular biology (Clifton, N.J.), Vol. 2105).

Bibtex

@inbook{2b5d5e4d16074e42a69ff15757132402,
title = "Facile Preparation of PNA-Peptide Conjugates with a Polar Maleimide-Thioether Linkage",
abstract = "Conjugation of a delivery peptide containing a thiol functionality (e.g., a cysteine residue) with a PNA oligomer displaying a single unprotected aliphatic primary amine (e.g., the N-terminus or a C-terminal lysine residue) can be achieved via a one-pot modification with a bisfunctional maleimide linker also displaying a reactive N-hydroxysuccinimidyl ester group (e.g., Mal-PEG2-OSu). Here, an optimized protocol with respect to ratios between the reactants as well as recommended reaction times is presented. Formation and conversion of the maleimide-PNA intermediate was followed by analytical HPLC as exemplified by its conjugation to (KFF)3K-Cys-NH2. In addition, the reaction time required for direct conversion of a preformed Mal-(CH2)2-(C=O)-PNA oligomer in the presence of a slight excess of thiol-modified peptide (with a varying degree of sterical hindrance: HS-(CH2)2-CONH-(KFF)3K-NH2, (KFF)3K-hCys-NH2 and (KFF)3K-Cys-NH2) is provided.",
author = "Hansen, {Anna Mette} and Shaikh, {Ashif Yasin} and Henrik Franzyk",
year = "2020",
doi = "10.1007/978-1-0716-0243-0_6",
language = "English",
isbn = "978-1-0716-0242-3",
series = "Methods in molecular biology (Clifton, N.J.)",
publisher = "Humana Press",
pages = "97--118",
editor = "{Peter E. Nielsen}",
booktitle = "Peptide Nucleic Acids",
address = "United States",

}

RIS

TY - CHAP

T1 - Facile Preparation of PNA-Peptide Conjugates with a Polar Maleimide-Thioether Linkage

AU - Hansen, Anna Mette

AU - Shaikh, Ashif Yasin

AU - Franzyk, Henrik

PY - 2020

Y1 - 2020

N2 - Conjugation of a delivery peptide containing a thiol functionality (e.g., a cysteine residue) with a PNA oligomer displaying a single unprotected aliphatic primary amine (e.g., the N-terminus or a C-terminal lysine residue) can be achieved via a one-pot modification with a bisfunctional maleimide linker also displaying a reactive N-hydroxysuccinimidyl ester group (e.g., Mal-PEG2-OSu). Here, an optimized protocol with respect to ratios between the reactants as well as recommended reaction times is presented. Formation and conversion of the maleimide-PNA intermediate was followed by analytical HPLC as exemplified by its conjugation to (KFF)3K-Cys-NH2. In addition, the reaction time required for direct conversion of a preformed Mal-(CH2)2-(C=O)-PNA oligomer in the presence of a slight excess of thiol-modified peptide (with a varying degree of sterical hindrance: HS-(CH2)2-CONH-(KFF)3K-NH2, (KFF)3K-hCys-NH2 and (KFF)3K-Cys-NH2) is provided.

AB - Conjugation of a delivery peptide containing a thiol functionality (e.g., a cysteine residue) with a PNA oligomer displaying a single unprotected aliphatic primary amine (e.g., the N-terminus or a C-terminal lysine residue) can be achieved via a one-pot modification with a bisfunctional maleimide linker also displaying a reactive N-hydroxysuccinimidyl ester group (e.g., Mal-PEG2-OSu). Here, an optimized protocol with respect to ratios between the reactants as well as recommended reaction times is presented. Formation and conversion of the maleimide-PNA intermediate was followed by analytical HPLC as exemplified by its conjugation to (KFF)3K-Cys-NH2. In addition, the reaction time required for direct conversion of a preformed Mal-(CH2)2-(C=O)-PNA oligomer in the presence of a slight excess of thiol-modified peptide (with a varying degree of sterical hindrance: HS-(CH2)2-CONH-(KFF)3K-NH2, (KFF)3K-hCys-NH2 and (KFF)3K-Cys-NH2) is provided.

U2 - 10.1007/978-1-0716-0243-0_6

DO - 10.1007/978-1-0716-0243-0_6

M3 - Book chapter

C2 - 32088866

SN - 978-1-0716-0242-3

SN - 978-1-0716-0245-4

T3 - Methods in molecular biology (Clifton, N.J.)

SP - 97

EP - 118

BT - Peptide Nucleic Acids

A2 - null, Peter E. Nielsen

PB - Humana Press

ER -

ID: 269722976