Synthesis of a tricyclic hexapeptide -via two consecutive ruthenium-catalyzed macrocyclization steps- with a constrained topology to mimic vancomycin?s binding properties toward D-Ala-D-Ala dipeptide

X. Yang; J. Kemmink; D.T.S. Rijkers; R.M.J. Liskamp

doi:10.1016/j.bmcl.2022.128887

Synthesis of a tricyclic hexapeptide -via two consecutive ruthenium-catalyzed macrocyclization steps- with a constrained topology to mimic vancomycin?s binding properties toward D-Ala-D-Ala dipeptide

X. Yang
, J. Kemmink
, D.T.S. Rijkers
, R.M.J. Liskamp^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › Academic › peer-review

Abstract

A ring-closing metathesis (RCM) - peptide coupling - ruthenium-catalyzed azide alkyne cycloaddition (RuAAC) strategy was developed to synthesize a tricyclic hexapeptide in which the side chain to side chain connectivity pattern resulted in a mimic with a topology that effectively mimics the bioactivity of vancomycin as a potent binder of the bacterial cell wall D-Ala-D-Ala dipeptide sequence and more importantly being an effective in-hibitor of bacterial growth.

Original language	English
Article number	128887
Number of pages	5
Journal	Bioorganic & Medicinal Chemistry Letters
Volume	73
DOIs	https://doi.org/10.1016/j.bmcl.2022.128887
Publication status	Published - 1 Oct 2022

Keywords

Macrocycles
Peptides
Peptidomimetics
Ring -closing metathesis
Ru-based azide alkyne cycloaddition
AZIDE-ALKYNE CYCLOADDITION
GLYCOPEPTIDE ANTIBIOTICS
TRIPEPTIDES
CYCLIZATION
PEPTIDES
REDESIGN
POCKET
SCOPE
CD

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Yang, X., Kemmink, J., Rijkers, D. T. S., & Liskamp, R. M. J. (2022). Synthesis of a tricyclic hexapeptide -via two consecutive ruthenium-catalyzed macrocyclization steps- with a constrained topology to mimic vancomycin?s binding properties toward D-Ala-D-Ala dipeptide. Bioorganic & Medicinal Chemistry Letters, 73, Article 128887. https://doi.org/10.1016/j.bmcl.2022.128887

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title = "Synthesis of a tricyclic hexapeptide -via two consecutive ruthenium-catalyzed macrocyclization steps- with a constrained topology to mimic vancomycin?s binding properties toward D-Ala-D-Ala dipeptide",

abstract = "A ring-closing metathesis (RCM) - peptide coupling - ruthenium-catalyzed azide alkyne cycloaddition (RuAAC) strategy was developed to synthesize a tricyclic hexapeptide in which the side chain to side chain connectivity pattern resulted in a mimic with a topology that effectively mimics the bioactivity of vancomycin as a potent binder of the bacterial cell wall D-Ala-D-Ala dipeptide sequence and more importantly being an effective in-hibitor of bacterial growth.",

keywords = "Macrocycles, Peptides, Peptidomimetics, Ring -closing metathesis, Ru-based azide alkyne cycloaddition, AZIDE-ALKYNE CYCLOADDITION, GLYCOPEPTIDE ANTIBIOTICS, TRIPEPTIDES, CYCLIZATION, PEPTIDES, REDESIGN, POCKET, SCOPE, CD",

author = "X. Yang and J. Kemmink and D.T.S. Rijkers and R.M.J. Liskamp",

note = "Funding Information: X.Y. acknowledges the China Scholarship Council (CRC) for financial support. We would like to thank, dr. Javier Sastre Tora{\~n}o for performing the HRMS analyses, Linda Quarles van Ufford for measuring the MIC values, and Hao Zhang for his help with the modeling experiments. Publisher Copyright: {\textcopyright} 2022 The Author(s)",

year = "2022",

month = oct,

day = "1",

doi = "10.1016/j.bmcl.2022.128887",

language = "English",

volume = "73",

journal = "Bioorganic \& Medicinal Chemistry Letters",

issn = "0960-894X",

publisher = "Elsevier Ltd",

}

Synthesis of a tricyclic hexapeptide -via two consecutive ruthenium-catalyzed macrocyclization steps- with a constrained topology to mimic vancomycin?s binding properties toward D-Ala-D-Ala dipeptide. / Yang, X.; Kemmink, J.; Rijkers, D.T.S. et al.
In: Bioorganic & Medicinal Chemistry Letters, Vol. 73, 128887, 01.10.2022.

Research output: Contribution to journal › Article › Academic › peer-review

TY - JOUR

T1 - Synthesis of a tricyclic hexapeptide -via two consecutive ruthenium-catalyzed macrocyclization steps- with a constrained topology to mimic vancomycin?s binding properties toward D-Ala-D-Ala dipeptide

AU - Yang, X.

AU - Kemmink, J.

AU - Rijkers, D.T.S.

AU - Liskamp, R.M.J.

N1 - Funding Information: X.Y. acknowledges the China Scholarship Council (CRC) for financial support. We would like to thank, dr. Javier Sastre Toraño for performing the HRMS analyses, Linda Quarles van Ufford for measuring the MIC values, and Hao Zhang for his help with the modeling experiments. Publisher Copyright: © 2022 The Author(s)

PY - 2022/10/1

Y1 - 2022/10/1

N2 - A ring-closing metathesis (RCM) - peptide coupling - ruthenium-catalyzed azide alkyne cycloaddition (RuAAC) strategy was developed to synthesize a tricyclic hexapeptide in which the side chain to side chain connectivity pattern resulted in a mimic with a topology that effectively mimics the bioactivity of vancomycin as a potent binder of the bacterial cell wall D-Ala-D-Ala dipeptide sequence and more importantly being an effective in-hibitor of bacterial growth.

AB - A ring-closing metathesis (RCM) - peptide coupling - ruthenium-catalyzed azide alkyne cycloaddition (RuAAC) strategy was developed to synthesize a tricyclic hexapeptide in which the side chain to side chain connectivity pattern resulted in a mimic with a topology that effectively mimics the bioactivity of vancomycin as a potent binder of the bacterial cell wall D-Ala-D-Ala dipeptide sequence and more importantly being an effective in-hibitor of bacterial growth.

KW - Macrocycles

KW - Peptides

KW - Peptidomimetics

KW - Ring -closing metathesis

KW - Ru-based azide alkyne cycloaddition

KW - AZIDE-ALKYNE CYCLOADDITION

KW - GLYCOPEPTIDE ANTIBIOTICS

KW - TRIPEPTIDES

KW - CYCLIZATION

KW - PEPTIDES

KW - REDESIGN

KW - POCKET

KW - SCOPE

KW - CD

U2 - 10.1016/j.bmcl.2022.128887

DO - 10.1016/j.bmcl.2022.128887

M3 - Article

C2 - 35835378

SN - 0960-894X

VL - 73

JO - Bioorganic & Medicinal Chemistry Letters

JF - Bioorganic & Medicinal Chemistry Letters

M1 - 128887

ER -

Synthesis of a tricyclic hexapeptide -via two consecutive ruthenium-catalyzed macrocyclization steps- with a constrained topology to mimic vancomycin?s binding properties toward D-Ala-D-Ala dipeptide

Abstract

Keywords

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