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A unique bacteriohopanetetrol stereoisomer of marine anammox

Lookup NU author(s): Dr Rachel Schwartz-Narbonne, Dr Alex Charlton, Dr Martin Jones, Dr Helen Talbot, Dr Darci Rush



This work is licensed under a Creative Commons Attribution 4.0 International License (CC BY 4.0).


Anaerobic ammonium oxidation (anammox) is a major process of bioavailable nitrogen removal from marine systems. Previously, a bacteriohopanetetrol (BHT) isomer, with unknown stereochemistry, eluting later than BHT when examined by high performance liquid chromatography (HPLC), was detected in ‘Ca. Scalindua profunda’ and proposed as a biomarker for anammox in marine paleo-environments. However, the utility of this BHT isomer as an anammox biomarker is hindered by the fact that four other, non-anammox, bacteria are also known to produce a late-eluting BHT stereoisomer. The stereochemistry in Acetobacter pasteurianus, Komagataeibacter xylinus and Frankia sp. was known to be 17β, 21β(H), 22R, 32R, 33R, 34R (BHT-34R). The stereochemistry of the late-eluting BHT in Methylocella palustris was unknown. To determine if marine anammox bacteria produce a unique BHT isomer, we studied the BHT distributions and stereochemistry of known BHT isomer producers and of previously unscreened marine (‘Ca. Scalindua brodeae’) and freshwater (‘Ca. Brocadia spp.’) anammox bacteria, using HPLC and gas chromatographiy (GC) analysis of acetylated BHTs and ultra high performance liquid chromatography (UHPLC)-high resolution mass spectrometry (HRMS) analysis of non-acetylated BHTs. The 34R stereochemistry was confirmed for the BHT isomers in Ca. Brocadia sp. and Methylocella palustris. However, ‘Ca. Scalindua spp.’ synthesises a stereochemically distinct BHT isomer, with still unconfirmed stereochemistry (BHT-x). Only GC analysis of acetylated BHT and UHPLC analysis of non-acetylated BHT distinguished between late-eluting BHT isomers. Acetylated BHT-x and BHT-34R co-elute when examined by HPLC. As BHT-x is currently only known to be produced by ‘Ca. Scalindua spp.’, it may be a biomarker for marine anammox.

Publication metadata

Author(s): Schwartz-Narbonne R, Schaeffer P, Hopmans EC, Schenesse M, Charlton EA, Jones DM, Sinninghe Damsté JS, Ul Haque MF, Jetten MSM, Lengger SK, Murrell CJ, Normand P, Nuijten GHL, Talbot HM, Rush D

Publication type: Article

Publication status: Published

Journal: Organic Geochemistry

Year: 2020

Volume: 143

Print publication date: 01/05/2020

Online publication date: 25/02/2020

Acceptance date: 21/02/2020

Date deposited: 22/05/2020

ISSN (print): 0146-6380

ISSN (electronic): 1873-5290

Publisher: Elsevier


DOI: 10.1016/j.orggeochem.2020.103994


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Funder referenceFunder name
NE/N011112/1Natural Environment Research Council (NERC)