Peptide Macrocycles Featuring a Backbone Secondary Amine: A Convenient Strategy for the Synthesis of Lipidated Cyclic and Bicyclic Peptides on Solid Support

Research output: Contribution to journal › Journal article › Research › peer-review

Standard

Peptide Macrocycles Featuring a Backbone Secondary Amine: A Convenient Strategy for the Synthesis of Lipidated Cyclic and Bicyclic Peptides on Solid Support. / Oddo, Alberto; Münzker, Lena; Hansen, Paul Robert.

In: Organic Letters, Vol. 17, No. 10, 2015, p. 2502-2505.

Research output: Contribution to journal › Journal article › Research › peer-review

Harvard

Oddo, A, Münzker, L & Hansen, PR 2015, 'Peptide Macrocycles Featuring a Backbone Secondary Amine: A Convenient Strategy for the Synthesis of Lipidated Cyclic and Bicyclic Peptides on Solid Support', Organic Letters, vol. 17, no. 10, pp. 2502-2505. https://doi.org/10.1021/acs.orglett.5b01026

APA

Oddo, A., Münzker, L., & Hansen, P. R. (2015). Peptide Macrocycles Featuring a Backbone Secondary Amine: A Convenient Strategy for the Synthesis of Lipidated Cyclic and Bicyclic Peptides on Solid Support. Organic Letters, 17(10), 2502-2505. https://doi.org/10.1021/acs.orglett.5b01026

Vancouver

Oddo A, Münzker L, Hansen PR. Peptide Macrocycles Featuring a Backbone Secondary Amine: A Convenient Strategy for the Synthesis of Lipidated Cyclic and Bicyclic Peptides on Solid Support. Organic Letters. 2015;17(10):2502-2505. https://doi.org/10.1021/acs.orglett.5b01026

Author

Oddo, Alberto ; Münzker, Lena ; Hansen, Paul Robert. / Peptide Macrocycles Featuring a Backbone Secondary Amine: A Convenient Strategy for the Synthesis of Lipidated Cyclic and Bicyclic Peptides on Solid Support. In: Organic Letters. 2015 ; Vol. 17, No. 10. pp. 2502-2505.

Bibtex

@article{91e53422556e49a1b33a62696d238da0,

title = "Peptide Macrocycles Featuring a Backbone Secondary Amine: A Convenient Strategy for the Synthesis of Lipidated Cyclic and Bicyclic Peptides on Solid Support",

abstract = "A convenient strategy for the on-resin synthesis of macrocyclic peptides (3- to 13-mers) via intramolecular halide substitution by a diamino acid is described. The method is compatible with standard Fmoc/tBu SPPS and affords a tail-to-side-chain macrocyclic peptide featuring an endocyclic secondary amine. This functional group is still reactive toward acylation, allowing for the continuation of the synthesis. An application to the synthesis of lipidated cyclic and bicyclic antimicrobial peptides is presented.",

author = "Alberto Oddo and Lena M{\"u}nzker and Hansen, {Paul Robert}",

year = "2015",

doi = "10.1021/acs.orglett.5b01026",

language = "English",

volume = "17",

pages = "2502--2505",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "10",

}

RIS

TY - JOUR

T1 - Peptide Macrocycles Featuring a Backbone Secondary Amine: A Convenient Strategy for the Synthesis of Lipidated Cyclic and Bicyclic Peptides on Solid Support

AU - Oddo, Alberto

AU - Münzker, Lena

AU - Hansen, Paul Robert

PY - 2015

Y1 - 2015

N2 - A convenient strategy for the on-resin synthesis of macrocyclic peptides (3- to 13-mers) via intramolecular halide substitution by a diamino acid is described. The method is compatible with standard Fmoc/tBu SPPS and affords a tail-to-side-chain macrocyclic peptide featuring an endocyclic secondary amine. This functional group is still reactive toward acylation, allowing for the continuation of the synthesis. An application to the synthesis of lipidated cyclic and bicyclic antimicrobial peptides is presented.

AB - A convenient strategy for the on-resin synthesis of macrocyclic peptides (3- to 13-mers) via intramolecular halide substitution by a diamino acid is described. The method is compatible with standard Fmoc/tBu SPPS and affords a tail-to-side-chain macrocyclic peptide featuring an endocyclic secondary amine. This functional group is still reactive toward acylation, allowing for the continuation of the synthesis. An application to the synthesis of lipidated cyclic and bicyclic antimicrobial peptides is presented.

U2 - 10.1021/acs.orglett.5b01026

DO - 10.1021/acs.orglett.5b01026

M3 - Journal article

C2 - 25923311

VL - 17

SP - 2502

EP - 2505

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 10

ER -

ID: 136841862