Cepaciachelin, A New Catecholate Siderophore From Burkholderia (Pseudomonas) Cepacia ***

1996 ◽  
Vol 51 (9-10) ◽  
pp. 627-630 ◽  
Author(s):  
I. Barelmann ◽  
J.-M. Meyer ◽  
K. Taraz ◽  
H. Budzikiewicz
Keyword(s):  
Chemical Degradation ◽  
Pseudomonas Cepacia ◽  
Spectroscopic Methods ◽  
First Case ◽  
Hydroxamate Siderophores

In addition to the known hydroxamate siderophores ornibactin C6 and C8 a catecholate siderophore named cepaciachelin, 1-N-[2-N′,6-N′-di(2,3-dihydroxybenzoyl)-ʟ-lysyl]-1,4-diaminobutane, was isolated from a Burkholderia (Pseudomonas) cepacia PHP7 culture and its structure elucidated by chemical degradation and spectroscopic methods. This is the first case of a member of the Pseudomonas group which produces both hydroxamate and catecholate siderophores

The Siderophores of Pseudomonas fluorescens 18.1 and the Importance of Cyclopeptidic Substructures for the Recognition at the Cell Surface

2000 ◽  
Vol 55 (9-10) ◽  
pp. 671-680 ◽  
Author(s):  
Cordula Amann ◽  
Kambiz Taraz ◽  
Herbert Budzikiewicz ◽  
Jean-Marie Meyer
Keyword(s):  
Cell Surface ◽  
Pseudomonas Fluorescens ◽  
Mutual Recognition ◽  
Chemical Degradation ◽  
Spectroscopic Methods

Abstract The structure of the pyoverdin siderophore of Pseudomonas fluorescens 18.1 was elucidated by spectroscopic methods and chemical degradation. By cross feeding studies structurally closely related pyoverdins containing a C-terminal cyclopeptidic substructure were tested regarding the mutual recognition by the producing strains. Partial recognition of foreign pyoverdins was observed.

A Pyoverdin from the Antarctica Strain 51W of Pseudomonas fluorescens

1999 ◽  
Vol 54 (3-4) ◽  
pp. 156-162 ◽  
Author(s):  
Jessica Voss ◽  
Kambiz Taraz ◽  
Herbert Budzikiewicz
Keyword(s):  
Amino Acids ◽  
Pseudomonas Fluorescens ◽  
Binding Sites ◽  
Chemical Shifts ◽  
Chemical Degradation ◽  
Spectroscopic Methods ◽  
Extreme Conditions ◽  
Structural Elements ◽  
Nmr Data ◽  
Schirmacher Oasis

From the strain 51W of Pseudomonas fluorescens living under extreme conditions at the Schirmacher Oasis (Antarctica) a pyoverdin was obtained. Its structure was elucidated by chemical degradation and spectroscopic methods. The NMR data of the pyoverdin and of its Ga(III) complex were compared. Appreciable influences of the metal on the chemical shifts of the atoms at its binding sites were observed. Thus the structural elements involved in the complexation can be identified and coinciding signals of amino acids occurring more than once in the peptide chain can be separated.

Structure Elucidation of Azotobactin 87, Isolated from Azotobacter vinelandii ATCC 12837*, **

1996 ◽  
Vol 51 (3-4) ◽  
pp. 139-150 ◽  
Author(s):  
E. M. Schaffner ◽  
R. Hartmann ◽  
K. Taraz ◽  
H. Budzikiewicz
Keyword(s):  
Structure Elucidation ◽  
Culture Medium ◽  
Azotobacter Vinelandii ◽  
2D Nmr ◽  
Chemical Degradation ◽  
Spectroscopic Methods ◽  
Hydroxybutyric Acid ◽  
Iron Deficient ◽  
N Terminus ◽  
Sequential Information

Abstract Chromopeptide siderophores (azotobactin 87-1 and -II) were isolated from an iron deficient culture medium of Azotobacter vinelandii ATCC 12837 (=DSM 87). Their structures were elu­ cidated by chemical degradation studies and spectroscopic methods, especially 2D-NMR-tech-niques. Total assignments of 1H-, 13C-, and 15N-resonances based on 2D-HOHAHA-, 1H/13C-HMQC-, 1H /13C-HMBC-, 1H /15N-HMQC/TOCSY-, and 1H/15N-HMBC-experiments are given as well as sequential information derived from 1H/1H-NOESY-, 1H /13C-HMBC-and 1H/ 13N-HMBC-experiments. Both Az 87-1 and Az 87-11 consist of a tetracyclic chromophore -(1S)8,9-dihydroxy-4-oxo-2,3,4,5-tetrahydro-1H,10cH-3a,5,10b-triazaacephenantrylene-1-carb-oxylic acid -and a decapeptide chain linked with the N-terminus to the carboxy group of the chromophore containing also modified, non-proteinogenic amino acids. The sequence L-Ser-D-Ser-L-Hse-Gly-D-threo-OHAsp-Hse-Hse-Hse-D-N5OH-N5-R-Hbu-Om-L-Hse was determined for Az 87-1, while Az 87-11 contains a C-terminal L-Hse-lactone instead. Iron is chelated by the catecholic group of the chromophore, the β-hydroxy aspartic acid, and the hydroxamate function formed by N5-hydroxyornithine and R-β-hydroxybutyric acid.

The chemical constituents of Australian Flindersia species. XIX. Triterpenoids from the leaves of F. bourjotiana F. Muell

1966 ◽  
Vol 19 (3) ◽  
pp. 455 ◽  
Author(s):  
GJW Breen ◽  
E Ritchie ◽  
WTL Sidwell ◽  
WC Taylor
Keyword(s):  
Chemical Constituents ◽  
Chemical Degradation ◽  
Spectroscopic Methods ◽  
The Absolute ◽  
Absolute Stereochemistry

From the leaves of Flindersia bourjotinna F. Muell. there were isolated sitosterol, triacontanol, lupeol, germanicol, germanicone, and four new triterpenoids, the bourjotinolones A, B, and C, and bourjotone. By chemical degradation and spectroscopic methods, the structures of these substances were shown to be 21,24-epoxy-23,25-dihydroxytirucall-7-en-3one, 23,24-dihydroxytirucalla-7,25-dien- 3-one, 25-chloro-23,24-dihydroxytirucall-7-en-3-one, and 25,26,27-trisnortirucall-7- ene-3,23-dione, respectively. Bourjotinolone C is almost certainly an artefact but bourjotinolone B and bourjotone are less likely to be. From biogenetic and N.M.R. spectral considerations, the absolute stereochemistry of the new triterpenes may be deduced.

Pigments of Fungi. LII Anisochiral Flavomannin 6,6′,8-Tri-O-methyl Ether from an Australian Dermocybe Toadstool

1999 ◽  
Vol 52 (8) ◽  
pp. 749 ◽  
Author(s):  
Malcolm S. Buchanan ◽  
Melvyn Gill ◽  
Alberto Gimenez ◽  
Somphone Phonh-Axa ◽  
Evelin Raudies ◽  
...  
Keyword(s):  
Natural Product ◽  
Methyl Ether ◽  
Absolute Configuration ◽  
Enantiomeric Purity ◽  
Chemical Degradation ◽  
Spectroscopic Methods ◽  
Fruiting Bodies ◽  
The Absolute

Flavomannin 6,6′,8-tri-O-methyl ether occurs in the fruiting bodies of the Australian toadstool Dermocybe sp. WAT 24274 as an anisochiral mixture of the (3S,3′S,P)- and (3R,3′R,M)-enantiomers (5) and (7), respectively, in which the former predominates to the extent of 50% e.e. The structure of the natural product is determined by spectroscopic methods and the absolute configuration and enantiomeric purity are deduced from the c.d. spectrum and by chemical degradation of the natural product to a mixture of stereoisomeric dihydroanthracenones that has been analysed by chiral h.p.l.c.

Chemical studies of the Proteaceae. I. Grevillea robusta A. Cunn, and Orites excelsa R. Br

1965 ◽  
Vol 18 (12) ◽  
pp. 2015 ◽  
Author(s):  
E Ritchie ◽  
WC Taylor ◽  
STK Vautin
Keyword(s):  
Chemical Degradation ◽  
High Yield ◽  
Spectroscopic Methods ◽  
Grevillea Robusta ◽  
Chemical Studies

From the wood of Grevillea robusta a new phenol, grevillol, was isolated in high yield, together with sitosterol. The structure of grevillol was established as 5-n-tridecylresorcinol by spectroscopic methods, chemical degradation, and synthesis. The wood of Orites excelsa yielded only sitosterol.

Staphyloferrin B, a Citrate Siderophore of Ralstonia eutropha

1999 ◽  
Vol 54 (11) ◽  
pp. 867-875 ◽  
Author(s):  
Maik Münzinger ◽  
Kambiz Taraz ◽  
Herbert Budzikiewicz
Keyword(s):  
Culture Medium ◽  
New Genus ◽  
Ralstonia Eutropha ◽  
Alcaligenes Eutrophus ◽  
Chemical Degradation ◽  
Spectroscopic Methods ◽  
Relationship Of ◽  
The Relationship

Abstract The structure and stereochemistry of the siderophore isolated from the culture medium of Ralstonia eutropha (formerly Alcaligenes eutrophus) could be elucidated as staphyloferrin B by spectroscopic methods and chemical degradation. The relationship of the three species of the new genus Ralstonia is reflected in the observation that all three form citrate sidero-phores.

Catecholate Siderophores from Chryseomonas luteola

1996 ◽  
Vol 51 (5-6) ◽  
pp. 281-285 ◽  
Author(s):  
M. Adolphs ◽  
K. Taraz ◽  
H. Budzikiewicz
Keyword(s):  
Culture Medium ◽  
2D Nmr ◽  
Chemical Degradation ◽  
Spectroscopic Methods ◽  
Iron Deficient ◽  
Nmr Techniques ◽  
Degradation Studies ◽  
Chryseomonas Luteola

Abstract Two catecholate siderophores (chrysobactin and chryseomonin) were isolated from an iron-deficient culture medium of Chryseomonas luteola. Their structures were elucidated by chemical degradation studies and spectroscopic methods, especially 2D-NMR techniques, and confirmed by synthesis. Chryseomonin constitutes a novel type of catecholate siderophore.

Achromobactin, a New Citrate Siderophore of Erwinia chrysanthemi

2000 ◽  
Vol 55 (5-6) ◽  
pp. 328-332 ◽  
Author(s):  
Maik Münzinger ◽  
Herbert Budzikiewicz ◽  
Dominique Expert ◽  
Corine Enard ◽  
Jean-Marie Meyer
Keyword(s):  
Culture Medium ◽  
Chemical Degradation ◽  
Erwinia Chrysanthemi ◽  
Spectroscopic Methods

The structure of a citrate siderophore named achromobactin isolated from the culture medium of Erwinia chrysanthemi was elucidated by spectroscopic methods and chemical degradation.

Chemical studies of the Proteaceae. IV. The structures of the major phenols of Grevillea striata; a group of novel cyclophanes

1970 ◽  
Vol 23 (1) ◽  
pp. 147 ◽  
Author(s):  
DD Ridley ◽  
E Ritchie ◽  
WC Taylor
Keyword(s):  
Double Bond ◽  
Structure Determination ◽  
Ring System ◽  
Chemical Degradation ◽  
Aliphatic Chain ◽  
Spectroscopic Methods ◽  
Ether Extract ◽  
Phenolic Fraction ◽  
Saturated Chain ◽  
Chemical Studies

Attempts to separate the major constituents of the phenolic fraction of the ether extract of the wood of Grevillea striata R.Br. were unsuccessful, but by chemical degradation and spectroscopic methods the structures of four of the components were deduced. They were mono- and di-methyl ethers of 17,19,22,24- tetrahydroxy(l4-p-0-o)cyclophane with a double bond at either of two positions in the aliphatic chain. The new ring system was given the trivial name "turriane". Evidence that a fifth and a sixth component were derivatives with a saturated chain, and a seventh was a derivative of a double homologue of turriane, was obtained. Synthetic experiments connected with the structure determination, and on the synthesis of tetrahydroxyturriane are described. Possible biogenetic routes to striatol and the cyclophanes are discussed.

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