Carboxylic acid replacement structure-activity relationships in suosan type sweeteners. A sweet taste antagonist. 1

Gw, Müller; Jc, Culberson; Roy, G.; Ziegler, J. B.; Walters, D. Eric; Ms, Kellogg; Ss, Schiffman; Zs, Warwick

doi:10.1021/jm00088a008

Cited by 13 publications

(4 citation statements)

References 6 publications

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“…β-alanine is an important β-amino acid, widely used in the food, chemical, and pharmaceutical industries. , Aspartate 1-decarboxylase (PanD) is the only enzyme capable of β-alanine synthesis in E . coli …”

Section: Resultsmentioning

confidence: 99%

“…49 β-alanine is an important β-amino acid, widely used in the food, chemical, and pharmaceutical industries. 50,51 Aspartate 1decarboxylase (PanD) is the only enzyme capable of β-alanine synthesis in E. coli. 52 L-Aspartate can be used as the main precursor to produce β-alanine by microbial fermentation, a process releasing one CO 2 .…”

Section: Design and Verification Of The New Acetyl-coamentioning

confidence: 99%

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Engineering a Novel Acetyl-CoA Pathway for Efficient Biosynthesis of Acetyl-CoA-Derived Compounds

Nie,

Wang,

Zhang

2023

ACS Synth. Biol.

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Acetyl-CoA is an essential central metabolite in living organisms and a key precursor for various value-added products as well. However, the intracellular availability of acetyl-CoA limits the efficient production of these target products due to complex and strict regulation. Here, we proposed a new acetyl-CoA pathway, relying on two enzymes, threonine aldolase and acetaldehyde dehydrogenase (acetylating), which can convert one L-threonine into one acetyl-CoA, one glycine, and generate one NADH, without carbon loss. Introducing the acetyl-CoA pathway could increase the intracellular concentration of acetyl-CoA by 8.6-fold compared with the wild-type strain. To develop a cost-competitive and genetically stable acetyl-CoA platform strain, the new acetyl-CoA pathway, driven by the constitutive strong promoter, was integrated into the chromosome of Escherichia coli. We demonstrated the practical application of this new acetyl-CoA pathway by high titer production of β-alanine, mevalonate, and N-acetylglucosamine. At the same time, this pathway achieved a high-yield production of glycine, a value-added commodity chemical for the synthesis of glyphosate and thiamphenicol. This work shows the potential of this new acetyl-CoA pathway for the industrial production of acetyl-CoA-derived compounds.

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Section: Resultsmentioning

confidence: 99%

Section: Design and Verification Of The New Acetyl-coamentioning

confidence: 99%

Engineering a Novel Acetyl-CoA Pathway for Efficient Biosynthesis of Acetyl-CoA-Derived Compounds

Nie,

Wang,

Zhang

2023

ACS Synth. Biol.

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“…The major disadvantage of the suosan sweetener family is their low water solubility, particularly at the pH used in carbonated beverages. A potential carboxylic acid metaphor is the use of a semisquarate derivative [139]. Incorporation of this highly acidic polar group, may well assist in the solubility of these new squarate sweeteners, in carbonated food preparations [140].…”

Section: Suosan Semisquaratementioning

confidence: 99%

Squaryl Molecular Metaphors – Application to Rational Drug Design and Imaging Agents

Kitson¹

2017

J Diagn Imaging Ther

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Molecular Metaphors is the application of squaryl building blocks towards creative functional group chemistry to produce lead compounds and imaging agents. This strategy is applied to rational drug design and to various imaging agents that would normally contain conventional functional group chemistry. These, include carboxylic acids, α-amino acids, peptide bonds and phosphonates. Moreover, the squaryl metaphor is a precursor to complex organic molecules involving functional group interchange (FGI) and rearrangements. This article discusses the application of these metaphors in the area of neurochemistry, especially NMDA receptors. An important area of drug design is the inhibition of angiotensin II enzyme by the use of losartan. This commercial drug contains a tetrazole moiety that can be modified using the squaryl group to give a semisquarate derivative. These concepts can extend to the semisquarate of ibuprofen. Moreover, a discussion on peptidomimetics regarding the substitution of the peptide bond for squaramide allows for a change in the biological properties due to modification at the peptide bond. Furthermore, the topic on how squaryl metaphors can be exploited primarily by the central 1,3-hydroxyamide sequence to the generation of a novel class of HIV protease inhibitors. Also, squaryl metaphors can be used to develop potential inhibitors of glutathione and novel anti-migraine drugs. The discussion continues on the design of anticancer drugs: in particular, a novel class of metalloproteases, including phosphonates for semisquaramides, leading to squaryl nucleosides. This review concludes with the application of squaryl metaphors in the design of positron emission tomography (PET) and magnetic resonance imaging (MRI) agents towards theranostics. describe the ability of individual functional chemical groups to mimic other moieties [2,3]. KeywordsErlenmeyer rationalised these concepts and categorised isosteres into atoms, ions and molecules based on the valence level of electrons [4]. A further understanding by Friedman led to the term bioisosterism to include all atoms and molecules that fit the broadest definition of isosteres [5]. This approach was independent of whether the drug was an agonist or an antagonist towards biological activity.Moreover, Thornber applied the term bioisosterism to include subunits, groups or molecules that possess physicochemical properties of similar biological effects [6]. Finally, in 1991 Burger widened the definition of bioisosteres to include compounds or groups that possess similar molecular shapes and volumes independent of agonists or antagonists [7]. REVIEW ARTICLE Squaryl KitsonThese bioisosteres would require approximately the same distribution of electrons and give a high probability of generating comparable physical properties such as hydrophobicity [8]. Currently, bioisosterism is one of the most useful tools to the medicinal chemist in rational drug design and in particular regarding the carboxylic acid bioisosteres [9]. The carboxylic acid functional ...

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“…1, capable of producing hydrogen bonded nanostructures. Although similar aromatic, sulfonate-urea compounds have been previously synthesised (Muller and co-workers, 29 Christensen and co-workers [30][31][32] ) the self-association properties of this class of compounds remains unexplored.…”

Section: Introductionmentioning

confidence: 99%

In situ modification of nanostructure configuration through the manipulation of hydrogen bonded amphiphile self-association

et al. 2016

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Herein, we report the synthesis of a novel amphiphilic salt containing a number of hydrogen bond donating (HBD) and accepting (HBA) functionalities. This amphiphile has been shown to self-associate via hydrogen bond formation in a DMSO solution, confirmed through a combination of NMR, UV-Vis and dynamic light scattering and supported by X-ray diffraction studies. The combination of different HBD and HBA functionalities within the amphiphile structure gives rise to a variety of competitive, self-associative hydrogen bonding modes that result in the formation of 'frustrated' hydrogen bonded nanostructures. These nanostructures can be altered through the addition of competitive HBD arrays and/or HBA anionic guests. The addition of these competitive species modifies the type of self-associative hydrogen bonding modes present between the amphiphilic molecules, triggering the in situ formation of novel hydrogen bonded nanostructures.

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Carboxylic acid replacement structure-activity relationships in suosan type sweeteners. A sweet taste antagonist. 1

Cited by 13 publications

References 6 publications

Engineering a Novel Acetyl-CoA Pathway for Efficient Biosynthesis of Acetyl-CoA-Derived Compounds

Engineering a Novel Acetyl-CoA Pathway for Efficient Biosynthesis of Acetyl-CoA-Derived Compounds

Squaryl Molecular Metaphors – Application to Rational Drug Design and Imaging Agents

In situ modification of nanostructure configuration through the manipulation of hydrogen bonded amphiphile self-association

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