Solid-phase synthesis of a peptide-based P,S-ligand system designed for generation of combinatorial catalyst libraries

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Standard

Solid-phase synthesis of a peptide-based P,S-ligand system designed for generation of combinatorial catalyst libraries. / Christensen, Christian A.; Meldal, Morten.

I: Journal of Combinatorial Chemistry, Bind 9, Nr. 1, 01.2007, s. 79-85.

Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt

Harvard

Christensen, CA & Meldal, M 2007, 'Solid-phase synthesis of a peptide-based P,S-ligand system designed for generation of combinatorial catalyst libraries', Journal of Combinatorial Chemistry, bind 9, nr. 1, s. 79-85. https://doi.org/10.1021/cc0600627

APA

Christensen, C. A., & Meldal, M. (2007). Solid-phase synthesis of a peptide-based P,S-ligand system designed for generation of combinatorial catalyst libraries. Journal of Combinatorial Chemistry, 9(1), 79-85. https://doi.org/10.1021/cc0600627

Vancouver

Christensen CA, Meldal M. Solid-phase synthesis of a peptide-based P,S-ligand system designed for generation of combinatorial catalyst libraries. Journal of Combinatorial Chemistry. 2007 jan.;9(1):79-85. https://doi.org/10.1021/cc0600627

Author

Christensen, Christian A. ; Meldal, Morten. / Solid-phase synthesis of a peptide-based P,S-ligand system designed for generation of combinatorial catalyst libraries. I: Journal of Combinatorial Chemistry. 2007 ; Bind 9, Nr. 1. s. 79-85.

Bibtex

@article{9561376bbad44e2783a0e8a92eae7c57,
title = "Solid-phase synthesis of a peptide-based P,S-ligand system designed for generation of combinatorial catalyst libraries",
abstract = "An efficient methodology for the solid-phase synthesis of diverse combinatorial peptide-based P,S-ligand libraries based on a modular approach was developed. Chiral thioethers were introduced into a series of peptide scaffolds using commercially available Fmoc-protected cysteine derivatives, and secondary amines were incorporated into the peptide backbones by reductive alkylation using readily available Fmoc-protected amino aldehydes. Phosphinylation of the secondary amines of the scaffolds, applying two different reagents, yielded two different types of ligands. Subsequent complexation with palladium afforded six- or seven-membered chelates, respectively. The selectivity, in an asymmetric allylic substitution reaction, of the two different types of chelates, derived from the same peptide scaffold, was complementary in all cases studied, affording the product as opposite stereoisomers with up to 60% ee. These results hold great promise for the identification of highly selective catalysts upon screening of larger P,S-based catalyst libraries.",
author = "Christensen, {Christian A.} and Morten Meldal",
year = "2007",
month = jan,
doi = "10.1021/cc0600627",
language = "English",
volume = "9",
pages = "79--85",
journal = "ACS Combinatorial Science",
issn = "2156-8952",
publisher = "ACS Publications",
number = "1",

}

RIS

TY - JOUR

T1 - Solid-phase synthesis of a peptide-based P,S-ligand system designed for generation of combinatorial catalyst libraries

AU - Christensen, Christian A.

AU - Meldal, Morten

PY - 2007/1

Y1 - 2007/1

N2 - An efficient methodology for the solid-phase synthesis of diverse combinatorial peptide-based P,S-ligand libraries based on a modular approach was developed. Chiral thioethers were introduced into a series of peptide scaffolds using commercially available Fmoc-protected cysteine derivatives, and secondary amines were incorporated into the peptide backbones by reductive alkylation using readily available Fmoc-protected amino aldehydes. Phosphinylation of the secondary amines of the scaffolds, applying two different reagents, yielded two different types of ligands. Subsequent complexation with palladium afforded six- or seven-membered chelates, respectively. The selectivity, in an asymmetric allylic substitution reaction, of the two different types of chelates, derived from the same peptide scaffold, was complementary in all cases studied, affording the product as opposite stereoisomers with up to 60% ee. These results hold great promise for the identification of highly selective catalysts upon screening of larger P,S-based catalyst libraries.

AB - An efficient methodology for the solid-phase synthesis of diverse combinatorial peptide-based P,S-ligand libraries based on a modular approach was developed. Chiral thioethers were introduced into a series of peptide scaffolds using commercially available Fmoc-protected cysteine derivatives, and secondary amines were incorporated into the peptide backbones by reductive alkylation using readily available Fmoc-protected amino aldehydes. Phosphinylation of the secondary amines of the scaffolds, applying two different reagents, yielded two different types of ligands. Subsequent complexation with palladium afforded six- or seven-membered chelates, respectively. The selectivity, in an asymmetric allylic substitution reaction, of the two different types of chelates, derived from the same peptide scaffold, was complementary in all cases studied, affording the product as opposite stereoisomers with up to 60% ee. These results hold great promise for the identification of highly selective catalysts upon screening of larger P,S-based catalyst libraries.

UR - http://www.scopus.com/inward/record.url?scp=33846610551&partnerID=8YFLogxK

U2 - 10.1021/cc0600627

DO - 10.1021/cc0600627

M3 - Journal article

C2 - 17206835

AN - SCOPUS:33846610551

VL - 9

SP - 79

EP - 85

JO - ACS Combinatorial Science

JF - ACS Combinatorial Science

SN - 2156-8952

IS - 1

ER -

ID: 321882818