Biosynthesis of streptothricin F. 5. Formation of .beta.-lysine by Streptomyces L-1689-23

Thiruvengadam, T. K.; Gould, Steven J.; Aberhart, D. John; Lin, Horng-Jau

doi:10.1021/ja00354a047

Cited by 41 publications

(18 citation statements)

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“…The structures of the physiological osmolytes synthesized by methanogens are (3-amino acids, unusual compounds that have rarely been described in biological systems. L-P3Glutamate has been detected and characterized (11,13) (1990) 9087 and is an important moiety in the formation of several antibiotics (23). The few other,-amino acids that have been detected occur almost exclusively in marine organisms.…”

Section: Discussionmentioning

confidence: 99%

N epsilon-acetyl-beta-lysine: an osmolyte synthesized by methanogenic archaebacteria.

Sowers

Robertson

Noll

et al. 1990

Proc. Natl. Acad. Sci. U.S.A.

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Methanosarcina thermophila, a nonmarine methanogenic archaebacterium, can grow in a range of saline concentrations. At less than 0.4 M NaCi, Ms. thermophila accumulated glutamate in response to increasing osmotic stress. At greater than 0.4 M NaCI, this organism synthesized a modified (3-amino acid that was identified as N6-acetyl-.8-lysine by NMR spectroscopy and ion-exchange HPLC.This (-amino acid derivative accumulated to high intracellular concentrations (up to 0.6 M) in Ms. thermophila and in another methanogen examined-Methanogenium cariaci, a marine species. The compound has features that are characteristic of a compatible solute: it is neutrally charged at physiological pH and it is highly soluble. When the cells were grown in the presence of exogenous glycine betaine, a physiological compatible solute, N6-acetyl--lysine synthesis was repressed and glycine betaine was accumulated. N8-Acetyl-(3-lysine was synthesized by species from three phylogenetic families when grown in high solute concentrations, suggesting that it may be ubiquitous among the methanogens. The ability to control the biosynthesis of N'-acetyl-(3-lysine in response to extracellular solute concentration indicates that the methanogenic archaebacteria have a unique (3amino acid biosynthetic pathway that is osmotically regulated.Microorganisms can proliferate in a diverse range of saline concentrations from low saline environments such as freshwater lakes to saturated brines found in solar salterns (1, 2). Cell size and the intracellular water activity must remain relatively constant to maintain physiological processes. Eukaryotic and eubacterial microorganisms have evolved mechanisms that enable them to minimize water loss when the extracellular solute concentration exceeds that of the cell cytoplasm (1-3). The mechanism of this adaptation involves the uptake or synthesis of low molecular weight organic compounds known as physiological compatible solutes (4, 5). These compounds reduce the osmotic potential between the extracellular milieu and the cytoplasm and protect enzymes from the low water activity that results from solute accumulation.Methanogenic archaebacteria have been isolated from environments with NaCl concentrations ranging from <0.05 M for many nonmarine species to >4 M for halophilic species (6). Individual species can also adapt to a range of saline concentrations. Methanosarcina thermophila, which was isolated from a thermophilic sludge digestor, grows in medium containing 0.05-1.2 M NaCl (7-9), and the marine species Methanogenium cariaci (10) grows in medium containing 0.17-1.4 M NaCl (D.N. and M.F.R., unpublished results). Compatible solutes have been detected in methanogenic bacteria (11-13). Several species of marine methanogens synthesize ,-glutamate in response to external NaCl (11, 13). Methanogens have also been reported to accumulate glycine betaine if it is provided in the medium (12). However, the mechanism for adaptation to high osmotic stress has not been investigated. Here we report the structure of ...

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Section: Discussionmentioning

confidence: 99%

N epsilon-acetyl-beta-lysine: an osmolyte synthesized by methanogenic archaebacteria.

Sowers

Robertson

Noll

et al. 1990

Proc. Natl. Acad. Sci. U.S.A.

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“…Streptothrisamine was generated by a de-acetylation step catalyzed by StnI. Feeding experiments have shown already that -lysines in ST are generated from L-Lys [8]. Accumulation of streptothrisamines in the ∆stnO mutant CIM1004 proved that StnO is the aminomutase responsible for this conversion.…”

Section: Discussionmentioning

confidence: 99%

“…It has been established that the -Lys residues in ST poly-β-Lys chain are derived from L-Lys [8]. Two incomplete ST clusters were cloned from Streptomyces rochei F20 and nourseothricin producer Streptomyces noursei [9,10].…”

mentioning

confidence: 99%

Mining of a streptothricin gene cluster from Streptomyces sp. TP-A0356 genome via heterologous expression

Guo

Huang

et al. 2013

Sci. China Life Sci.

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“…For example, β-lysine is a precursor for the biosynthesis of antibiotics viomycin and streptothricin in Streptomyces (3,4).β-Lysine is also the intermediate for the complete catabolism of lysine to carbon dioxide, ammonia and water in Clostridium subterminale SB4 (5,6).…”

Section: Introductionmentioning

confidence: 99%

Basis for the equilibrium constant in the interconversion of l-lysine and l-β-lysine by lysine 2,3-Aminomutase

Chen

Tanem

Frey

2007

Biochimica et Biophysica Acta (BBA) - Proteins and Proteomics

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SUMMARYL-β-Lysine and β-glutamate are produced by the actions of lysine 2,3-aminomutase and glutamate 2,3-aminomutase, respectively. The pK a values compounds have been titrimetrically measured and are for L-β-lysine: pK 1 = 3.25 (carboxyl), pK 2 = 9.30 (β-aminium), and pK 3 = 10.5 (ε-aminium). For β-glutamate the values are pK 1 = 3.13 (carboxyl), pK 2 = 3.73 (carboxyl), and pK 3 = 10.1 (β-aminium). The equilibrium constants for reactions of 2,3-aminomutases favor the β-isomers. The pH-and temperature dependencies of K eq have been measured for the reaction of lysine 2,3-aminomutase to determine the basis for preferential formation of β-lysine. The value of K eq (8.5 at 37 °C) is independent of pH between pH 6 and pH 11; ruling out differences in pK-values as the basis for the equilibrium constant. The K eq -value is temperature-dependent and ranges from 10.9 at 4 °C to 6.8 at 65 °C. The linear van't Hoff plot shows the reaction to be enthalpy-driven, with ΔH° = −1.4 kcal mol −1 and ΔS° = −0.25 cal deg −1 mol −1 . Exothermicity is attributed to the greater strength of the bond C β -N β in L-β-lysine than C α -N α in L-lysine, and this should hold for other amino acids.

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Biosynthesis of streptothricin F. 5. Formation of .beta.-lysine by Streptomyces L-1689-23

Cited by 41 publications

References 0 publications

N epsilon-acetyl-beta-lysine: an osmolyte synthesized by methanogenic archaebacteria.

N epsilon-acetyl-beta-lysine: an osmolyte synthesized by methanogenic archaebacteria.

Mining of a streptothricin gene cluster from Streptomyces sp. TP-A0356 genome via heterologous expression

Basis for the equilibrium constant in the interconversion of l-lysine and l-β-lysine by lysine 2,3-Aminomutase

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