<scp>L</scp>-Serine methyl ester hydrochloride

Schouten, Arie; Lutz, Martin

doi:10.1107/s1600536809046480

Cited by 2 publications

(1 citation statement)

References 10 publications

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“…1) has been published previously. 15 Bond distances and bond angles for Boc-BrAlaMe and BrAlaMe are essentially identical, and the experimental bond distances and angles for BrAlaMe also agree with the calculated ones. On the other hand, the dihedral angles measured and calculated, respectively, for BrAlaMe clearly differ from each other in particular in the surroundings of the chiral centre C1: While the carbonyl group and nitrogen are in the same plane (∠O1C2-C1N1 = 179°) in the solid state structure, the respective angle in the calculated gas-phase structure is 118°.…”

Section: Resultssupporting

confidence: 67%

Modelling the site of bromide binding in vanadate-dependent bromoperoxidases

Kraehmer

Rehder

2012

Dalton Trans.

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Treatment of Boc-protected (S)-serine (Ser) methyl ester with triphenylphosphine bromide Ph(3)PBr (intermittently generated from PPh(3) and N-bromosuccinimide) yields Boc-3-bromoalanine (R)-Boc-BrAlaMe and, after deprotection, bromoalanine methyl ester (R)-BrAlaMe in the form of its hydrobromide. Boc-BrAlaMe and BrAlaMe have been structurally characterised. The reaction between BrAlaMe, salicylaldehyde (sal) and VO(2+) results in the formation of Schiff base complexes of composition [VO(sal-BrAlaMe)solv](+) (solv = CH(3)OH: 3, THF: 5) and [VO(sal-BrAla)THF] 4. DFT calculations of the structures of 3, 4 and 5, based on the B3LYP functional and employing the triple zeta basis set 6-311++g(d,p), provide distances Br···V = 4.0 ± 0.1 Å, if some distortion of the dihedral angle ∠N-C-C-Br is allowed (affording a maximum energy of ca. 45 kJ mol(-1)), and thus model Br···V distances detected by X-ray methods in bromoperoxidases from the marine algae Ascophyllum nodosum and Corallina pilulifera. The DFT calculations have been validated by comparing calculated and found structures, including the new complex [V(V)O(Amp-sal)OMe(MeOH)] (1, Amp is the aminophenol moiety) and the known complex [VO(L-Ser-van)H(2)O] (van = vanillin). Additional validation has been undertaken by checking experimental against calculated (BHandHLYP) EPR spectroscopic hyperfine coupling constants. Complexes containing bromine as a substituent at the phenyl moiety of a Schiff base ligand do not allow for an appropriate simulation of the Br···V distance in peroxidases. The closest agreement, d(Br···V) = 4.87 Å, is achieved with [VO(3Br-salSer)THF] (6), where 3Brsal-Ser is the dianionic Schiff base formed between 3-Br-5-NO(2)-salicylaldehyde and serine.

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Section: Resultssupporting

confidence: 67%

Modelling the site of bromide binding in vanadate-dependent bromoperoxidases

Kraehmer

Rehder

2012

Dalton Trans.

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L-Alanine methyl ester hydrochloride monohydrate

Lutz

Schouten

2011

Acta Cryst E

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The enantiopure title compound, C4H10NO2 +·Cl−·H2O, forms a two-dimensional network by intermolecular hydrogen bonding parallel to (010). Non-merohedral twinning with a twofold rotation about the reciprocal c* axis as twin operation was taken into account during intensity integration and structure refinement. This twinning leads to alternative orientations of the stacked hydrogen-bonded layers.

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L-Serine methyl ester hydrochloride

Abstract: In the enantiopure crystal of the title compound, C4H10NO3 +·Cl−, intermolecular O—H⋯Cl and N—H⋯Cl hydrogen bonds link the molecules into layers parallel to (001).

Cited by 2 publications

References 10 publications

Modelling the site of bromide binding in vanadate-dependent bromoperoxidases

Modelling the site of bromide binding in vanadate-dependent bromoperoxidases

L-Alanine methyl ester hydrochloride monohydrate

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L-Serine methyl ester hydrochloride

Abstract: In the enanti­opure crystal of the title compound, C4H10NO3 +·Cl−, inter­molecular O—H⋯Cl and N—H⋯Cl hydrogen bonds link the mol­ecules into layers parallel to (001).

Cited by 2 publications

References 10 publications

Modelling the site of bromide binding in vanadate-dependent bromoperoxidases

Modelling the site of bromide binding in vanadate-dependent bromoperoxidases

L-Alanine methyl ester hydrochloride monohydrate

Contact Info

Product

Resources

About

Abstract: In the enantiopure crystal of the title compound, C4H10NO3 +·Cl−, intermolecular O—H⋯Cl and N—H⋯Cl hydrogen bonds link the molecules into layers parallel to (001).