Isolation and Synthesis of Glycophospholipids from the extremophile Chthonomonas calidirosea. Issue 11 (23rd September 2020)

• Record Type: Journal Article
• Authors: Compton, Benjamin J.; Lagutin, Kirill; Dyer, Blake S.; Ryan, Jason; MacKenzie, Andrew; Stott, Matthew B.; Nekrasov, Eduard V.; Painter, Gavin F.; Vyssotski, Mikhail
• Is Part Of: Asian journal of organic chemistry. Volume 9:Issue 11(2020)
• Page Start: 1802
• Page End: 1814
• Publication Date: 2020-09-23
• Subjects: Glycophospholipid -- Chthonomonas calidirosea -- hydroxylated alkylamine -- diastereoselectivity -- total synthesis; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.202000357
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract: An interesting set of ten phospholipids including eight previously unreported compounds have been isolated from the extremophile Chthonomonas calidirosea (strain T49 T ). Common within these metabolites is the phosphatidylglyceroylalkylamine core unit with the newly identified compounds containing α‐linked glucosyl, xylosyl or N ‐alanylglucosaminyl monosaccharides. The previously reported N ‐acetylglucosaminyl and aglycone derivatives were also identified in extracts from this bacterium. All metabolites were accompanied by a structural isomer which was shown to contain an extra hydroxyl group within the alkylamine chain. The absolute regio‐ and stereochemistries of the major phospholipids were confirmed by total synthesis. Abstract : Cultivation of the extremophilic bacterium Chthonomonas calidirosea (strain T49 T ) has led to the isolation of ten compounds incorporating a phosphatidylglyceroylalkylamine core unit, eight of which have not been previously reported. The absolute regio‐ and stereochemistries of the major phospholipids were confirmed by total synthesis.