Efficient total syntheses and biological activities of two teixobactin analogues. Issue 36 (17th March 2016)

• Record Type: Journal Article
• Authors: Parmar, Anish; Iyer, Abhishek; Vincent, Charlotte S.; Van Lysebetten, Dorien; Prior, Stephen H.; Madder, Annemieke; Taylor, Edward J.; Singh, Ishwar
• Is Part Of: Chemical communications. Volume 52:Issue 36(2016)
• Page Start: 6060
• Page End: 6063
• Publication Date: 2016-03-17
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/c5cc10249a
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : Efficient total syntheses of teixobactin analogues and their structure activity relationships are reported. The advantages of the synthetic approach are a high yield (22% for analogue1 ), key step of the macrocyclisation achieved in 60 minutes. Abstract : The discovery of the new antibiotic teixobactin has been timely in the race for unearthing novel antibiotics wherein the emergence of drug resistant bacteria poses a serious threat worldwide. Herein, we present the total syntheses and biological activities of two teixobactin analogues. This approach is simple, efficient and has several advantages: it uses commercially available building blocks (except AllocHN-d -Thr-OH), has a single purification step and a good recovery (22%). By using this approach we have synthesised two teixobactin analogues and established that thed -amino acids are critical for the antimicrobial activity of these analogues. With continuing high expectations from teixobactin, this work can be regarded as a stepping stone towards an in depth study of teixobactin, its analogues and the quest for synthesising similar molecules.