An electronic circular dichroism spectroscopy method for the quantification of L- and D-amino acids in enantiomeric mixtures

Ding, Ruiwen; Ying, Jianxi; Zhao, Yufen

doi:10.1098/rsos.201963

Cited by 6 publications

(3 citation statements)

References 29 publications

(32 reference statements)

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“…The structures of the cyclic dipeptides were elucidated by 1D and 2D NMR as well as corroborated with the literature (Table S1 and Figure S2A) [26][27][28][29][30]. Comparison of the CD spectra of compounds 2 to 5 (Figure S2B) to those found in the literature followed the 2S,2 ′ S (3S,6S for 2 to 4 and 3S,8aS for 5 in their IUPAC nomenclature) [31][32][33][34].…”

Section: Mzminesupporting

confidence: 84%

Targeted Isolation of Antibiofilm Compounds from Halophytic Endophyte Bacillus velezensis 7NPB-3B Using LC-HR-MS-Based Metabolomics

Singh,

Nwagwu,

Young

et al. 2024

Microorganisms

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The discovery of new natural products has become more challenging because of the re-isolation of compounds and the lack of new sources. Microbes dwelling in extreme conditions of high salinity and temperature are huge prospects for interesting natural metabolites. In this study, the endophytic bacteria Bacillus velezensis 7NPB-3B isolated from the halophyte Salicornia brachiata was screened for its biofilm inhibition against methicillin-resistant Staphylococcus aureus (MRSA). The fractionation of the crude extract was guided by bioassay and LC-HRMS-based metabolomics using multivariate analysis. The 37 fractions obtained by high-throughput chromatography were dereplicated using an in-house MS-Excel macro coupled with the Dictionary of Natural Products database. Successive bioactivity-guided separation yielded one novel compound (1), a diketopiperazine (m/z 469.258 [M − H]−) with an attached saturated decanoic acid chain, and four known compounds (2–5). The compounds were identified based on 1D- and 2D-NMR and mass spectrometry. Compounds 1 and 5 exhibited excellent biofilm inhibition properties of >90% against the MRSA pathogen at minimum inhibition concentrations of 25 and 35 µg/mL, respectively. The investigation resulted in the isolation of a novel diketopiperazine from a bacterial endophyte of an untapped plant using an omics approach.

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Section: Mzminesupporting

confidence: 84%

Targeted Isolation of Antibiofilm Compounds from Halophytic Endophyte Bacillus velezensis 7NPB-3B Using LC-HR-MS-Based Metabolomics

Singh,

Nwagwu,

Young

et al. 2024

Microorganisms

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“…The CD spectrum of l ‐Ala, l ‐Val, l ‐Ile, and l ‐Leu amino acids are characterized by a positive maximum at approximately 200 nm, which has been ascribed to the higher‐energy π → π* transition of the carbonyl group chromophore 18 . Their mirror‐image enantiomers, that is, d ‐Ala, d ‐Val, d ‐Ile, and d ‐Leu, thus display a mirrored spectrum that is reflected on the y axis, thus with a negative minimum in the same region 19 . However, in the case of aliphatic dipeptides, such as l ‐Ala‐ l ‐Ala, the situation is inverted 20 .…”

Section: Resultsmentioning

confidence: 99%

“…18 Their mirror-image enantiomers, that is, D-Ala, D-Val, D-Ile, and D-Leu, thus display a mirrored spectrum that is reflected on the y axis, thus with a negative minimum in the same region. 19 However, in the case of aliphatic dipeptides, such as L-Ala-L-Ala, the situation is inverted. 20 Furthermore, the presence of a lowerenergy n !…”

Section: Dipeptides Characterization and Selfassemblymentioning

confidence: 99%

Self‐assembly of heterochiral, aliphatic dipeptides with Leu

Scarel,

De Corti,

Polentarutti

et al. 2023

Journal of Peptide Science

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This work describes the self‐assembly behavior of heterochiral, aliphatic dipeptides, l‐Leu‐d‐Xaa (Xaa = Ala, Val, Ile, Leu), in green solvents such as acetonitrile (MeCN) and buffered water at neutral pH. Interestingly, water plays a structuring role because at 1% v/v, it enables dipeptide self‐assembly in MeCN to yield organogels, which then undergo transition towards crystals. Other organic solvents and oils were tested for gelation, and metastable gels were formed in tetrahydrofuran, although at high peptide concentration (80 mM). Single‐crystal X‐ray diffraction revealed the dipeptides' supramolecular packing modes in amphipathic layers, as opposed to water channels reported for the homochiral Leu–Leu, or hydrophobic columns reported for homochiral Leu–Val and Leu–Ile.

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Advances in Chiral Metabolomic Profiling and Biomarker Discovery

Pandey,

Tiziani

2024

Methods in Molecular Biology

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An electronic circular dichroism spectroscopy method for the quantification of L- and D-amino acids in enantiomeric mixtures

Cited by 6 publications

References 29 publications

Targeted Isolation of Antibiofilm Compounds from Halophytic Endophyte Bacillus velezensis 7NPB-3B Using LC-HR-MS-Based Metabolomics

Targeted Isolation of Antibiofilm Compounds from Halophytic Endophyte Bacillus velezensis 7NPB-3B Using LC-HR-MS-Based Metabolomics

Self‐assembly of heterochiral, aliphatic dipeptides with Leu

Advances in Chiral Metabolomic Profiling and Biomarker Discovery

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