Neotame: Synthesis, Stereochemistry and Sweetness

Prakash, Indra; Bishay, Ihab E.; Schroeder, Steve A.

doi:10.1080/00397919908086610

Cited by 16 publications

(10 citation statements)

References 2 publications

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“…The present method is rapid, sensitive, and reproducible with shorter migration times (Prakash et al 1999;Yang and Chen 2010). Lower detection limits were achieved in this method in contrast to previously reported methods (Hu et al NEOTAME BY CAPILLARY ELECTROPHORESIS 2805 2013; Matsumoto et al 2008;National Standard Method of China 2009;Yang and Chen 2010), as shown in Table 3.…”

Section: Performance Of the Present Methods With Reported Methodscontrasting

confidence: 66%

“…The performance of the developed method was compared with previously reported methods (Matsumoto et al 2008;Prakash et al 1999;Yang and Chen 2010). The present method is rapid, sensitive, and reproducible with shorter migration times (Prakash et al 1999;Yang and Chen 2010).…”

Section: Performance Of the Present Methods With Reported Methodsmentioning

confidence: 97%

“…Neotame has two chiral centers at the C 3 and C 5 positions; hence, it can form four diastereomers, namely L,L; L,D; D,D; and D,L neotame, and their sweetness is attributed to the presence of well-oriented hydrophobic groups in the L,L-diastereomer (Prakash et al 1999).…”

Section: Introductionmentioning

confidence: 99%

“…Due to the presence of amino acids and organic groups, neotame exhibits high sweeteness nearly 10,000 times sweeter than sugar and 40 times more sweeter than aspartame (Prakash, Bishay, and Schroeder 1999). Neotame has two chiral centers at the C 3 and C 5 positions; hence, it can form four diastereomers, namely L,L; L,D; D,D; and D,L neotame, and their sweetness is attributed to the presence of well-oriented hydrophobic groups in the L,L-diastereomer (Prakash et al 1999).…”

Section: Introductionmentioning

confidence: 99%

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Determination of Neotame by High-Performance Capillary Electrophoresis Using ß-cyclodextrin as a Chiral Selector

et al. 2014

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An electrokinetic chromatographic method was developed for the chiral separation of neotame, a new high intensity artificial sweetener, using a chiral separating agent heptakis 2,3,6-tri-o-methylbetacyclodextrin. The purpose of this study was to better understand diastereomer-resolution interactions between neotame and the chiral separating agent. Molecular docking studies were performed to elucidate the mechanism of the separation. The optimum conditions were 50 mM phosphate buffer, pH 5.5, applied voltage 20 kV, cassette temperature of 30 C, and a 4 s sample injection time. The calibration curve showed good linearity (r 2 > 0.99) with recoveries for both diastereomers, ranging from 95.66-99.00% and the limits of detection for L,L-neotame and D,D-neotame were 0.01857 and 0.08214 mM, respectively. The developed method showed analytical precision with relative standard deviations (n ¼ 5) of 1.20% and 1.17% with respect to migration time and peak area, respectively. A large difference in the interaction energies observed between the diastereomers represents a significant differentiation. The results showed that both electrostatic and hydrophobic interactions played a significant role in stabilizing their inclusion complexes and consequently supported the elution order based on their differential stabilities.

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Section: Performance Of the Present Methods With Reported Methodscontrasting

confidence: 66%

Section: Performance Of the Present Methods With Reported Methodsmentioning

confidence: 97%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Determination of Neotame by High-Performance Capillary Electrophoresis Using ß-cyclodextrin as a Chiral Selector

et al. 2014

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“…The sweetness of neotame is 8000 times more potent than sucrose, and approximately 40 times the sweetness potency of aspartame. 2 The most stable known crystal form of neotame under ambient conditions is the monohydrate. 3 Anhydrous neotame is capable of existing in several polymorphic forms and as an amorphous form.…”

Section: Introductionmentioning

confidence: 99%