1H NMR studies of rotational isomerism in phosphonic analogues of aspartic acid

drzejczyk, Danuta J; Ziora, Zyta M.; Kafarski, P

doi:10.1002/1097-458x(200005)38:5<370::aid-mrc651>3.0.co;2-m

Cited by 2 publications

(3 citation statements)

References 15 publications

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“…The NMR spectra of (±)‐ and ( R )‐ 10 were identical and identical to one in the literature but different to another one. 1 H NMR (400.13 MHz, D 2 O): δ = 3.71 (ddd, J = 14.0, 10.2, 3.7 Hz, 1 H, CHP), 3.05 (A part of ABX‐sys, J AB = 18.0, J = 8.6, J = 3.7 Hz, 1 H, CH 2 ), 2.85 (B part of ABX‐sys, J AB = 18.0, J = 10.2, J = 7.1 Hz, 1 H, CH 2 ) ppm.…”

Section: Methodssupporting

confidence: 63%

“…The organic layer was separated and the aqueous one was extracted with CH 2 Cl 2 (2 × 10 mL [α] D 25 = -33.6 (c = 1.0, water)}. The NMR spectra of (±)-and (R)-10 were identical and identical to one in the literature [32] but different [33] to another one. 1 21.31, H 4.77, N 8.28; found for (±)-10: C 21.38, H 4.90, N 8.05; found for (R)-10: C 21.46, H 4.68, N 8.15.…”

Section: Preparation Of Enantiomerically Pure (R)-(-)-diisopropyl 1-hmentioning

confidence: 97%

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Chemoenzymatic Synthesis of Racemic and Enantiomerically Pure Phosphaaspartic Acid and Phosphaarginine

et al. 2017

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Diisopropyl allyloxymethylphosphonate prepared by a one‐pot procedure was isomerized to give racemic 1‐hydroxy‐3‐butenylphosphonate with LDA by a [2,3]‐sigmatropic rearrangement. Chloroacetylation delivered an ester, which was resolved in a two‐phase system by using the lipase from Thermomyces lanuginosus. Racemic and (S)‐α‐hydroxyphosphonate 6 were converted to (±)‐ and (R)‐phosphaaspartic acid by functional‐group manipulation. (±)‐, (R)‐ and (S)‐6 were first esterified with 4‐nitrobenzenesulfonyl chloride before hydroboration to transform the double bond into a hydroxyethyl group. The hydroxyl group was manipulated to give a guanidinyl group and the 4‐nitrobenzenesulfonyloxy to give an amino group. Global deprotection of the α‐aminophosphonates yielded the desired phosphaamino acids.

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Section: Methodssupporting

confidence: 63%

Section: Preparation Of Enantiomerically Pure (R)-(-)-diisopropyl 1-hmentioning

confidence: 97%

Chemoenzymatic Synthesis of Racemic and Enantiomerically Pure Phosphaaspartic Acid and Phosphaarginine

et al. 2017

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“…The values found were and [83,84]. These limiting values were also recently used in the analysis of phosphonic acid analogues of aspartic acid and asparagine [94,95].…”

Section: Amino Acids and Their Derivativesmentioning

confidence: 96%

Determination of rotamer populations and related parameters from NMR coupling constants: a critical review

Kraszni

Szakács²,

Noszál³

2004

Analytical and Bioanalytical Chemistry

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Methods to determine rotamer populations from NMR homo- and heteronuclear vicinal coupling constants are reviewed. Theory and practice related to the elucidation of various gauche and trans limiting coupling constants as key parameters in the characterization of discrete rotational isomers are discussed. Properties and capacities of Karplus-type equations are assessed. Continuous models of rotational isomerism are compared to discrete ones. Principles of the highly specific physicochemical parameters rotamer-specific basicity and rotamer-specific partition coefficient are also described.

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1H NMR studies of rotational isomerism in phosphonic analogues of aspartic acid

Cited by 2 publications

References 15 publications

Chemoenzymatic Synthesis of Racemic and Enantiomerically Pure Phosphaaspartic Acid and Phosphaarginine

Chemoenzymatic Synthesis of Racemic and Enantiomerically Pure Phosphaaspartic Acid and Phosphaarginine

Determination of rotamer populations and related parameters from NMR coupling constants: a critical review

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