Breakdown of 3-(allylsulfonio)propanoates in bacteria from the Roseobacter group yields garlic oil constituents

Two analogues of 3-(dimethylsulfonio)propanoate (DMSP), 3-(diallylsulfonio)propanoate (DAllSP), and 3-(allylmethylsulfonio)propanoate (AllMSP), were synthesized and fed to marine bacteria from the Roseobacter clade. These bacteria are able to degrade DMSP into dimethyl sulfide and methanethiol. The DMSP analogues were also degraded, resulting in the release of allylated sulfur volatiles known from garlic. For unknown compounds, structural suggestions were made based on their mass spectrometric fragmentation pattern and confirmed by the synthesis of reference compounds. The results of the feeding experiments allowed to conclude on the substrate tolerance of DMSP degrading enzymes in marine bacteria.

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Synthesis and mass spectrometric fragmentation pattern of 6-(4-chlorophenyl)-N-aryl-4-(trichloromethyl)-4H-1,3,5-oxadiazin-2-amines

Heterocyclic Communications ◽

10.1515/hc-2018-0082 ◽

2018 ◽

Vol 24 (5) ◽

pp. 273-278 ◽

Cited By ~ 2

Author(s):

Pavlo V. Zadorozhnii ◽

Vadym V. Kiselev ◽

Ihor O. Pokotylo ◽

Oxana V. Okhtina ◽

Aleksandr V. Kharchenko

Keyword(s):

Mass Spectra ◽

Fast Atom Bombardment ◽

Mass Spectrometric ◽

Fragmentation Pattern ◽

Mass Spectrometric Fragmentation

Abstract The mass spectrometric fragmentation of 6-(4-chlorophenyl)-N-aryl-4-(trichloromethyl)-4H-1,3,5-oxadiazin-2-amines was studied under fast-atom bombardment (FAB) conditions. To simplify the interpretation of the mass spectra, a number of new 4H-1,3,5-oxadiazine derivatives containing polyisotopic elements (Cl and Br) in the arylamine substituent were synthesized. It was shown that fragmentation occurs in two main patterns.

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Structure proposal for a new pyoverdin from a ThaiPseudomonas putidastrain1

Spectroscopy An International Journal ◽

10.1155/2004/394872 ◽

2004 ◽

Vol 18 (3) ◽

pp. 453-458 ◽

Cited By ~ 6

Author(s):

Chalerm Ruangviriyachai ◽

Diana Uría Fernández ◽

Mathias Schäfer ◽

Herbert Budzikiewicz

Keyword(s):

Amino Acids ◽

Pseudomonas Putida ◽

Primary Structure ◽

Mass Spectrometric ◽

Fragmentation Pattern ◽

Mass Spectrometric Fragmentation

From a ThaiPseudomonas putidastrain a pyoverdin was isolated whose primary structure was deduced from its mass spectrometric fragmentation pattern. It belongs to the smallest representatives of this group of siderophores comprising only six amino acids.

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Structure Proposal for a New Pyoverdin from Pseudomonas sp. PS 6.10

Zeitschrift für Naturforschung C ◽

10.1515/znc-2006-11-1208 ◽

2006 ◽

Vol 61 (11-12) ◽

pp. 815-820 ◽

Cited By ~ 5

Author(s):

Herbert Budzikiewicz ◽

Mathias Schäfer ◽

Diana Uría Fernández ◽

Jean-Marie Meyer

Keyword(s):

Amino Acids ◽

Amino Acid ◽

Primary Structure ◽

Minimal Medium ◽

Mass Spectrometric ◽

Casamino Acid ◽

Fragmentation Pattern ◽

Pseudomonas Sp ◽

Mass Spectrometric Fragmentation ◽

Biogenetic Precursor

Abstract From Pseudomonas sp. PS 6.10, when grown in a casamino acid medium, a pyoverdin was isolated whose primary structure could be deduced from its mass spectrometric fragmentation pattern and amino acid analysis. It belongs to the smallest representatives of this group of siderophores comprising only six amino acids in its peptide chain. When grown in a succinate minimal medium the corresponding ferribactin considered to be the biogenetic precursor of the pyoverdin was obtained as the major component.

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