Microscale CD method for determining absolute configurations of acyclic amino tetrols and amino pentols. Structures of aminobacteriohopanepolyols from the methylotrophic bacterium Methylococcus luteus

Zhou, Peng; Berova, N.; Nakanishi, Koji; Knani, M'hamed; Rohmer, Michel

doi:10.1021/ja00010a082

Cited by 52 publications

(25 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…An aminotriol was the major hopanoid in Methylosinus trichosporium [14]. Hopanoids possessing an aminotetrol or aminopentol side chains were previously detected in two other species of methanotrophic bacteria : Methylomonas methanica and Methylococcus capsulatus [8] and Methylococcus luteus [9,10] (Table 1). The three latter ones are phylogenetically close to the Methylocaldum species.…”

Section: Resultsmentioning

confidence: 98%

Bacterial triterpenoids of the hopane series from the methanotrophic bacteria Methylocaldum spp.: phylogenetic implications and first evidence for an unsaturated aminobacteriohopanepolyol

Cvejić¹

2000

FEMS Microbiology Letters

View full text Add to dashboard Cite

The hopanoid content of the two methanotrophic bacteria Methylocaldum szegediense and Methylocaldum tepidum was investigated. 35-Aminobacteriohopane-30R,31R,32R,33S,34S-pentol and its 3L-methyl homologue were present in both strains. In M. tepidum, they were accompanied by 35-aminobacteriohopane-31R,32R,33S,34S-tetrol and its 3L-methyl homologue. The side chain structure was identical to those previously reported from two other obligate methanotrophs, Methylococcus capsulatus and Methylomonas methanica. The two Methylocaldum species shared with the Methylococcus species the presence of 3L-methylhopanoid as well as of a hopanoid releasing adiantol upon H 5 IO 6 /NaBH 4 treatment. A rare feature was in addition found in M. szegediense. The saturated hopanoids were accompanied by an unsaturated aminobacteriohopanepentol with a v 11 double bond. Comparison of the hopanoid fingerprints was in accordance with the close phylogenetic relationship of Methylococcus and Methylocaldum. The major difference was the absence of sterols in Methylocaldum which were always detected in the Methylococcus species. ß

show abstract

Section: Resultsmentioning

confidence: 98%

Bacterial triterpenoids of the hopane series from the methanotrophic bacteria Methylocaldum spp.: phylogenetic implications and first evidence for an unsaturated aminobacteriohopanepolyol

Cvejić¹

2000

FEMS Microbiology Letters

View full text Add to dashboard Cite

show abstract

“…All BHP side structures shown (III, IV, V) have previously been unambiguously identified by NMR and side chain stereogenic centres determined by ORD measurements for all three mentioned aminopolyols (Zhou et al, 1991). When identified in this study using LC-MS only, where stereochemistry cannot be confirmed, we have assumed the structure to be the same as that previously characterised but the occurrence of additional/alternative isomers cannot be excluded.…”

Section: Appendix Amentioning

confidence: 54%

“…Neunlist and Rohmer, 1985a;Zhou et al, 1991;Cvejic et al, 2000;Talbot et al, 2001;van Winden et al, 2012a). Two other aminoBHPs are commonly reported including the pentafunctionalised 35-aminobacteriohopane-31,32,33,34-tetrol (V; aminotetrol), produced by most Type I and II methanotrophs (Neunlist and Rohmer, 1985a,b;Cvejic et al, 2000;Talbot et al, 2001) with the exception of the Type II genera Methylocella (van Winden et al, 2012a,b).…”

Section: Biological Sources and Lipid Compositionmentioning

confidence: 99%

Synthesising bushmeat research effort in West and Central Africa: A new regional database

Taylor

Scharlemann

Rowcliffe

et al. 2015

Biological Conservation

View full text Add to dashboard Cite

Methane (CH 4 ) is a strong greenhouse gas known to have perturbed global climate in the past, especially when released in large quantities over short time periods from continental or marine sources. It is therefore crucial to understand and, if possible, quantify the individual and combined response of these variable methane sources to natural climate variability. However, past changes in the stability of greenhouse gas reservoirs remain uncertain and poorly constrained by geological evidence. Here, we present a record from the Congo fan of a highly specific bacteriohopanepolyol (BHP) biomarker for aerobic methane oxidation (AMO), 35-aminobacteriohopane-30,31,32,33,34-pentol (aminopentol), that identifies discrete periods of increased AMO as far back as 1.2 Ma. Fluctuations in the concentration of aminopentol, and other 35-aminoBHPs, follow a pattern that correlates with late Quaternary glacial-interglacial climate cycles, with highest concentrations during warm periods. We discuss possible sources of aminopentol, and the methane consumed by the precursor methanotrophs, within the context of the Congo River setting, including supply of methane oxidation markers from terrestrial watersheds and/or marine sources (gas hydrate and/or deep subsurface gas reservoir). Compound-specific carbon isotope values of À30& to À40& for BHPs in ODP 1075 and strong similarities between the BHP signature of the core and surface sediments from the Congo estuary and floodplain wetlands from the interior of the Congo River Basin, support a methanotrophic and likely terrigenous origin of the 35-aminoBHPs found in the fan sediments. This new evidence supports a causal connection between marine sediment BHP records of tropical deep sea fans and wetland settings in the feeding river catchments, and thus tropical continental hydrology. Further research is needed to better constrain the different sources and pathways of methane emission. However, this study identifies the large potential of aminoBHPs, in particular aminopentol, to trace and, once better calibrated and understood, quantify past methane sources and fluxes from terrestrial and potentially also marine sources.

show abstract

“…Interestingly, compounds 1 -4 ( Fig. 1) have been isolated from several different bacterial strains, and proved identical even in their side-chain configuration [6]. The relative and absolute configurations of the side chain of aminobacteriohopanetetrol ( ¼ (1R,2R,3S,4S)-5-amino-1-[(22R)-hopan-30-yl]pentane-1,2,3,4-tetrol; 1) and aminobacteriohopanepentol have been established by circular-dichroism (CD) experiments [6].…”

mentioning

confidence: 99%

“…1) have been isolated from several different bacterial strains, and proved identical even in their side-chain configuration [6]. The relative and absolute configurations of the side chain of aminobacteriohopanetetrol ( ¼ (1R,2R,3S,4S)-5-amino-1-[(22R)-hopan-30-yl]pentane-1,2,3,4-tetrol; 1) and aminobacteriohopanepentol have been established by circular-dichroism (CD) experiments [6]. However, their structures have never been confirmed by total or partial synthesis, which contrasts with biohopanoids that are not hydroxylated at C(31), whose structures had been corroborated by multi-step synthesis [10] [11].…”

mentioning

confidence: 99%

Diastereoselective Synthesis of Aminobacteriohopanetetrol, a Biomarker for Methanotrophic Bacteria: Confirmation of the Absolute Configuration

Pan¹,

Zhang²,

Guang-yi³

et al. 2007

Chemistry & Biodiversity

Self Cite

View full text Add to dashboard Cite

A short and convenient strategy was developed for the first stereoselective chemical synthesis of aminobacteriohopanetetrol (= (1R,2R,3S,4S)-5-amino-1-[(22R)-hopan-30-yl]pentane-1,2,3,4-tetrol; 1), a typical biomarker for methanotrophic bacteria. Comparison of the NMR spectra of the synthetic and natural (peracetylated) product enabled us to unambiguously corroborate the absolute configuration of the functionalized pentyl side chain of 1.

show abstract

Microscale CD method for determining absolute configurations of acyclic amino tetrols and amino pentols. Structures of aminobacteriohopanepolyols from the methylotrophic bacterium Methylococcus luteus

Cited by 52 publications

References 0 publications

Bacterial triterpenoids of the hopane series from the methanotrophic bacteria Methylocaldum spp.: phylogenetic implications and first evidence for an unsaturated aminobacteriohopanepolyol

Bacterial triterpenoids of the hopane series from the methanotrophic bacteria Methylocaldum spp.: phylogenetic implications and first evidence for an unsaturated aminobacteriohopanepolyol

Synthesising bushmeat research effort in West and Central Africa: A new regional database

Diastereoselective Synthesis of Aminobacteriohopanetetrol, a Biomarker for Methanotrophic Bacteria: Confirmation of the Absolute Configuration

Contact Info

Product

Resources

About