Serratamic acid, a derivative of <scp>l</scp>-serine produced by organisms of the <i>Serratia</i> group

Cartwright, N. J.

doi:10.1042/bj0600238

Cited by 31 publications

(6 citation statements)

References 6 publications

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“…This slow conversion presumably depends on the pH of the solution, as it was not found in all cases. Such an explanation is compatible with the first report of the lipoamino acid, serratamic acid, isolated from alkaline extraction of S. marcescens cultures, , as 1 has been shown to yield serratamic acid on mild alkaline hydrolysis. In keeping with this, two ring-opened compounds each corresponding to the addition of one molecule of water to serratamolides B ( 2 ) and D ( 4 ) were characterized by mass spectrometry.…”

Section: Resultssupporting

confidence: 89%

Antimycobacterial Serratamolides and Diacyl Peptoglucosamine Derivatives from Serratia sp.

et al. 2008

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The cyclodepsipeptide serratamolide A ( 1) and five closely related compounds together with three new glucosamine derivatives were isolated by bioactivity-guided chromatography from the XAD adsorber resin extract of a Serratia sp. The structures of the compounds were elucidated by 2D NMR and MS analyses. In addition to the known serratamolide A ( 1) with two C 10 alkyl chains, its derivatives always contained one C 10 chain combined with either C 12:1, C 12, C 11, C 9, or C 8 chains. The glucosamine derivatives contained a common core consisting of an N-butyl-alpha-glucopyranosylamide, which was acylated at the C-1 oxygen with valine. The differences between the derivatives arise from the nature of the acyl groups attached to the N-terminus of valine, which were identified as the linear fatty acid moieties C 16:1, C 15, or C 14. Each compound was present in two isomeric forms arising from racemization of the valine moiety. All compounds showed antibiotic activity against Mycobacterium diernhoferi and other rapidly growing mycobacteria.

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Section: Resultssupporting

confidence: 89%

Antimycobacterial Serratamolides and Diacyl Peptoglucosamine Derivatives from Serratia sp.

et al. 2008

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“…Large trays covered with solid medium, a method used with considerable success in this department for cultivating Serratia spp. (Cartwright, 1955), did not give much growth with the present organisms and there was no improvement when the agar was well-washed.…”

Section: R B Cainmentioning

confidence: 67%

The Microbial Metabolism of Nitro-aromatic Compounds

Cain

1958

Journal of General Microbiology

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“…The values of resonances corresponding to various absorption bands for all the NAGs are given in Table S1, Supporting Information. 1 H NMR spectra of NAGs showed resonances at 2.15−2.24 δ (2H, t) and 1.55−1.62 δ (2H, m) for the methylene groups at α and β positions to the amide carbonyl, respectively. Resonances were seen at 3.91−4.22 δ (2H, s) for the methylene group in the glycine moiety and at 6.16−6.92 δ (1H, bs) for the amide N−H.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Structure and Thermotropic Phase Behavior of a Homologous Series of N-Acylglycines: Neuroactive and Antinociceptive Constituents of Biomembranes

Reddy

Krovi

Swamy

2014

Crystal Growth & Design

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N-Acylglycines (NAGs) with different acyl chains have been found in the mammalian brain and other tissues. They exhibit significant biological and pharmacological properties and appear to play important roles in communication and signaling pathways within and between cells. In view of this, a homologous series of NAGs have been synthesized and characterized in the present study. Differential scanning calorimetric (DSC) studies show that the transition enthalpies and entropies of dry as well as hydrated NAGs exhibit a linear dependence on the acyl chain length. Most of the NAGs show a minor transition below the chain-melting phase transition, suggesting the presence of polymorphism in the solid state. Structures of N-myristoylglycine (NMG) and N-palmitoylglycine (NPG) were solved in monoclinic system with C2/c and P21 space groups, respectively. Analysis of the crystal structures show that NAGs are organized in a bilayer fashion, with head-to-head (and tail-to-tail) arrangement of molecules. The acyl chains in both structures are essentially perpendicular to the bilayer plane, which is consistent with a lack of odd–even alternation in the thermodynamic properties. The bilayer is stabilized by strong hydrogen bonding interactions between −COOH groups of the molecules from opposite leaflets as well as N–H···O hydrogen bonds between the amide groups of adjacent molecules in the same leaflet and dispersion interactions among the acyl chains. Powder X-ray diffraction data show that the d-spacings for the NAGs with different acyl chains (n = 8–20) exhibit a linear dependence on the chain length, suggesting that all the NAGs investigated here adopt a similar packing arrangement in the crystal lattice. These observations are relevant for understanding the role of N-acylglycines in biological membranes.

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Serratamic acid, a derivative of l-serine produced by organisms of the Serratia group

Cited by 31 publications

References 6 publications

Antimycobacterial Serratamolides and Diacyl Peptoglucosamine Derivatives from Serratia sp.

Antimycobacterial Serratamolides and Diacyl Peptoglucosamine Derivatives from Serratia sp.

The Microbial Metabolism of Nitro-aromatic Compounds

Structure and Thermotropic Phase Behavior of a Homologous Series of N-Acylglycines: Neuroactive and Antinociceptive Constituents of Biomembranes

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