The impact of backbone N-methylation on the structure-activity relationship of Leu10 -teixobactin

Journal of Peptide Science : an Official Publication of the European Peptide Society
Tony VelkovJohn A Karas

Abstract

Antimicrobial resistance is a serious threat to global human health; therefore, new anti-infective therapeutics are required. The cyclic depsi-peptide teixobactin exhibits potent antimicrobial activity against several Gram-positive pathogens. To study the natural product's mechanism of action and improve its pharmacological properties, efficient chemical methods for preparing teixobactin analogues are required to expedite structure-activity relationship studies. Described herein is a synthetic route that enables rapid access to analogues. Furthermore, our new N-methylated analogues highlight that hydrogen bonding along the N-terminal tail is likely to be important for antimicrobial activity.

References

Apr 25, 2000·Accounts of Chemical Research·S WendebornS Berteina
Jul 19, 2008·Accounts of Chemical Research·Jayanta ChatterjeeHorst Kessler
Jan 24, 2009·The Journal of Biological Chemistry·Karen S HarrisMichael Foley
Jan 7, 2015·Nature·Losee L LingKim Lewis
Dec 15, 2015·Organic Letters·Yahya E JadFernando Albericio
Mar 18, 2016·Chemical Communications : Chem Comm·Anish ParmarIshwar Singh
May 19, 2016·Organic Letters·Andrew M GiltrapRichard J Payne
May 28, 2016·ACS Chemical Biology·Hyunjun YangJames S Nowick
Aug 4, 2016·Nature Communications·Kang JinXuechen Li
Aug 11, 2017·Journal of Medicinal Chemistry·Shimaa A H Abdel MonaimBeatriz G de la Torre
Sep 29, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Shimaa A H Abdel MonaimBeatriz G de la Torre
Oct 11, 2017·Chemistry : a European Journal·Chuchu GuoQi Zhang
Oct 11, 2017·Organic & Biomolecular Chemistry·Christian E SchumacherMargaret A Brimble
Oct 17, 2017·Bioorganic & Medicinal Chemistry·Shimaa A H Abdel MonaimFernando Albericio
Mar 13, 2018·Biopolymers·Anamika SharmaFernando Albericio
Oct 9, 2018·Journal of the American Chemical Society·Hyunjun YangJames S Nowick

❮ Previous
Next ❯

Citations

Dec 4, 2019·Annals of the New York Academy of Sciences·John A KarasTony Velkov
Jun 11, 2020·Journal of Medicinal Chemistry·Vidya B GunjalD Srinivasa Reddy

❮ Previous
Next ❯

Related Concepts

Related Feeds

Antifungals

An antifungal, also known as an antimycotic medication, is a pharmaceutical fungicide or fungistatic used to treat and prevent mycosis such as athlete's foot, ringworm, candidiasis, cryptococcal meningitis, and others. Discover the latest research on antifungals here.

Antifungals (ASM)

An antifungal, also known as an antimycotic medication, is a pharmaceutical fungicide or fungistatic used to treat and prevent mycosis such as athlete's foot, ringworm, candidiasis, cryptococcal meningitis, and others. Discover the latest research on antifungals here.