Absolute configuration of natural methionine sulfoximine

Chevrier, Bernard; Moras, Dino; Jeannoda, Victor; Creppy, E. E.; Dirheimer, G.

doi:10.1107/s0108270186091205

Cited by 5 publications

(6 citation statements)

References 7 publications

(7 reference statements)

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“…a formal electron count of 48 for 1, would imply the nitrogen cap to act as a five-electron donor ligand [N --S + OMePh)], however, no 5e-µ 3 -NR cap has been reported so far. 4 Furthermore, the lack of two electrons with respect to the effective atomic number rule is in accordance with the structural data of 1 (Figure 2): The sulfur-nitrogen bond in (R)-1 (1.566 Å) lies within the range of NdS double bonds; in comparison with methionylsulfoximine (1.529 Å), 12 the sulfur-nitrogen distance in (R)-1 is only slightly longer.…”

supporting

confidence: 82%

[(μ₂-H)Ru₃(CO)₉{μ₃-NS(O)MePh}]: An Electron-Deficient Trinuclear Cluster Containing a Chiral Sulfoximido Cap

Süß‐Fink¹,

Rheinwald²,

Stœckli-Evans³

et al. 1996

Inorg. Chem.

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The chiral sulfoximine MePhS(O)NH reacts with [Ru3(CO)12] to give, with N−H activation and coordination of the H and NS(O)MePh fragments to the trinuclear ruthenium framework, the 46 electron cluster [(μ2-H)Ru3(CO)9{μ3-NS(O)MePh}] (1) which, in accordance with its electron-deficiency, takes up carbon monoxide reversibly to give the electron-precise 48 electron cluster [(μ2-H)Ru3(CO)10{μ2-NS(O)MePh}] (2).

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supporting

confidence: 82%

[(μ₂-H)Ru₃(CO)₉{μ₃-NS(O)MePh}]: An Electron-Deficient Trinuclear Cluster Containing a Chiral Sulfoximido Cap

Süß‐Fink¹,

Rheinwald²,

Stœckli-Evans³

et al. 1996

Inorg. Chem.

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“…In addition, the δ-amino group of Asn264 hydrogen bonds with the other carboxylate oxygen of Glu327 (5). The rest of the sulfonimide group is modeled using the crystal structure of MetSox (37). The O -S-N angle of 120°places the O atom in proximity to the Mn469 ion, with the protonated N atom oriented directly toward Glu327.…”

Section: Discussionmentioning

confidence: 99%

The Crystal Structure of Phosphinothricin in the Active Site of Glutamine Synthetase Illuminates the Mechanism of Enzymatic Inhibition

2001

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Phosphinothricin is a potent inhibitor of the enzyme glutamine synthetase (GS). The resolution of the native structure of GS from Salmonella typhimurium has been extended to 2.5 A resolution, and the improved model is used to determine the structure of phosphinothricin complexed to GS by difference Fourier methods. The structure suggests a noncovalent, dead-end mechanism of inhibition. Phosphinothricin occupies the glutamate substrate pocket and stabilizes the Glu327 flap in a position which blocks the glutamate entrance to the active site, trapping the inhibitor on the enzyme. One oxygen of the phosphinyl group of phosphinothricin appears to be protonated, because of its proximity to the carboxylate group of Glu327. The other phosphinyl oxygen protrudes into the negatively charged binding pocket for the substrate ammonium, disrupting that pocket. The distribution of charges in the glutamate binding pocket is complementary to those of phosphinothricin. The presence of a second ammonium binding site within the active site is confirmed by its analogue thallous ion, marking the ammonium site and its protein ligands. The inhibition of GS by methionine sulfoximine can be explained by the same mechanism. These models of inhibited GS further illuminate its catalytic mechanism.

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“…In addition n-hentriacontane has also shown analgesic and diuretic activities (Meyre-Silva et al, 1998;Rizvi et al, 1985). Moreover, rouremin (glycoside) isolated in R. minor has presented antimalarial activity (Bero et al, 2009;Chevrier et al, 1986;Grosvenor et al, 1995;He et al, 2006;Kalegari, 2009).…”

Section: Function Of Plants In Strict Dietsmentioning

confidence: 93%

Plant use in the medicinal practices known as “strict diets” in Chazuta valley (Peruvian Amazon)

Sanz‐Biset

Cañigueral

2011

Journal of Ethnopharmacology

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Absolute configuration of natural methionine sulfoximine

Cited by 5 publications

References 7 publications

[(μ₂-H)Ru₃(CO)₉{μ₃-NS(O)MePh}]: An Electron-Deficient Trinuclear Cluster Containing a Chiral Sulfoximido Cap

[(μ₂-H)Ru₃(CO)₉{μ₃-NS(O)MePh}]: An Electron-Deficient Trinuclear Cluster Containing a Chiral Sulfoximido Cap

The Crystal Structure of Phosphinothricin in the Active Site of Glutamine Synthetase Illuminates the Mechanism of Enzymatic Inhibition

Plant use in the medicinal practices known as “strict diets” in Chazuta valley (Peruvian Amazon)

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Absolute configuration of natural methionine sulfoximine

Cited by 5 publications

References 7 publications

[(μ2-H)Ru3(CO)9{μ3-NS(O)MePh}]: An Electron-Deficient Trinuclear Cluster Containing a Chiral Sulfoximido Cap

[(μ2-H)Ru3(CO)9{μ3-NS(O)MePh}]: An Electron-Deficient Trinuclear Cluster Containing a Chiral Sulfoximido Cap

The Crystal Structure of Phosphinothricin in the Active Site of Glutamine Synthetase Illuminates the Mechanism of Enzymatic Inhibition

Plant use in the medicinal practices known as “strict diets” in Chazuta valley (Peruvian Amazon)

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Product

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[(μ₂-H)Ru₃(CO)₉{μ₃-NS(O)MePh}]: An Electron-Deficient Trinuclear Cluster Containing a Chiral Sulfoximido Cap

[(μ₂-H)Ru₃(CO)₉{μ₃-NS(O)MePh}]: An Electron-Deficient Trinuclear Cluster Containing a Chiral Sulfoximido Cap