The favored formation of d,l-arabinitol in the formose reaction

Shigemasa, Yoshihiro; Matsuba, Akira; Ueda, Nasuo; Nakashima, Ruka; Harada, Kenichi; Takeda, Nobuhiro; Suzuki, Makoto; Saitô, Seiki

doi:10.1016/0008-6215(84)85034-x

Cited by 13 publications

(4 citation statements)

References 16 publications

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“…[4] Butlerov proposed am echanism for the reaction, [4a] which consisted of the following steps:t wo formaldehyde molecules condensed to form glycolaldehyde( GA), which reactedt hrough an aldol reaction with another equivalent of formaldehyde to afford glyceraldehyde (GLA). [7] However,a pplications of the formose reaction to important chemicals, with the exception of saccharide synthesis, have not been reported,t ot he best of our knowledge.S trict control of the formose reaction, that is, the coupling frequency of formaldehyde andt he handling of product mixtures, appears to be ac onsiderable issue. [7] However,a pplications of the formose reaction to important chemicals, with the exception of saccharide synthesis, have not been reported,t ot he best of our knowledge.S trict control of the formose reaction, that is, the coupling frequency of formaldehyde andt he handling of product mixtures, appears to be ac onsiderable issue.…”

Section: Introductionmentioning

confidence: 96%

“…[5] The aldoseketose isomerization of GLA forms 1,3-dihydroxyacetone (DHA), which can react with formaldehyde, GA, and GLA;s ubsequent isomerization results in the formation of tetrose,p entose, and hexose, respectively.T od ate, successful examples of the formose reaction, developed exclusively for the selective syntheses of unprotected sugars, have been carried out under either ab ase [6] or mineral. [7] However,a pplications of the formose reaction to important chemicals, with the exception of saccharide synthesis, have not been reported,t ot he best of our knowledge.S trict control of the formose reaction, that is, the coupling frequency of formaldehyde andt he handling of product mixtures, appears to be ac onsiderable issue.…”

Section: Introductionmentioning

confidence: 96%

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Mechanistic Insight into a Sugar‐Accelerated Tin‐Catalyzed Cascade Synthesis of α‐Hydroxy‐γ‐butyrolactone from Formaldehyde

et al. 2015

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Applications of the formose reaction, which involves the formation of sugars from formaldehyde, have previously been confined to the selective synthesis of unprotected sugars. Herein, it is demonstrated that α-hydroxy-γ-butyrolactone (HBL), which is one of the most important intermediates in pharmaceutical syntheses, can be produced from paraformaldehyde. In the developed reaction system, homogeneous tin chloride exhibits high catalytic activity and the addition of mono- and disaccharides accelerates the formation of HBL. These observations suggest that the formose reaction may serve as a feasible pathway for the synthesis of important chemicals.

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Section: Introductionmentioning

confidence: 96%

Section: Introductionmentioning

confidence: 96%

Mechanistic Insight into a Sugar‐Accelerated Tin‐Catalyzed Cascade Synthesis of α‐Hydroxy‐γ‐butyrolactone from Formaldehyde

et al. 2015

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“…Most notably, the reaction generates a plethora of unstable sugars, of which the key sugar, ribose, is present in a very small proportion (17)(18)(19). Although the problem of sugar instability is unresolved, some molecules, such as borates, phosphates, and cyanamide, select for the synthesis of certain sugars (20)(21)(22)(23)(24). All these reactions require alkaline conditions such as those found naturally in hydrothermal vents, in some lakes, and at the surfaces of aluminosilicate minerals (25)(26)(27).…”

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confidence: 99%

The Silicate-Mediated Formose Reaction: Bottom-Up Synthesis of Sugar Silicates

Lambert

Andavan

2010

Science

149

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Understanding the mechanism of sugar formation and stabilization is important for constraining theories on the abiotic origin of complex biomolecules. Although previous studies have produced sugars from small molecules through the formose and related reactions, the product mixtures are complex and unstable. We have demonstrated that simple two- and three-carbon molecules (glycolaldehyde and glyceraldehyde), in the presence of aqueous sodium silicate, spontaneously form silicate complexes of four- and six-carbon sugars, respectively. Silicate selects for sugars with a specific stereochemistry and sequesters them from rapid decomposition. Given the abundance of silicate minerals, these observations suggest that formose-like reactions may provide a feasible pathway for the abiotic formation of biologically important sugars, such as ribose.

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“…The oligomerization of aldehyde is the basic reaction of the formose reaction in which diverse lengths of sugars and sugar-related compounds form 60 . The formose reaction is also known to form many sugar-related compounds, including sugar alcohols and sugar acids, and diverse CHO compounds 61 , 62 . Reactions between aldehydes and ammonia are known to form IOM-like matter with carboxylic acids, amines, sugars, and amino acids 15 , 17 , 21 .…”

Section: Discussionmentioning

confidence: 99%

Distributions of CHN compounds in meteorites record organic syntheses in the early solar system

Furukawa

Saigusa

Kano

et al. 2023

Sci Rep

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Carbonaceous meteorites contain diverse soluble organic compounds. These compounds formed in the early solar system from volatiles accreted on tiny dust particles. However, the difference in the organic synthesis on respective dust particles in the early solar system remains unclear. We found micrometer-scale heterogeneous distributions of diverse CHN1-2 and CHN1-2O compounds in two primitive meteorites: the Murchison and NWA 801, using a surface-assisted laser desorption/ionization system connected to a high mass resolution mass spectrometer. These compounds contained mutual relationships of ± H2, ± CH2, ± H2O, and ± CH2O and showed highly similar distributions, indicating that they are the products of series reactions. The heterogeneity was caused by the micro-scale difference in the abundance of these compounds and the extent of the series reactions, indicating that these compounds formed on respective dust particles before asteroid accretion. The results of the present study provide evidence of heterogeneous volatile compositions and the extent of organic reactions among the dust particles that formed carbonaceous asteroids. The compositions of diverse small organic compounds associated with respective dust particles in meteorites are useful to understand different histories of volatile evolution in the early solar system.

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The favored formation of d,l-arabinitol in the formose reaction

Cited by 13 publications

References 16 publications

Mechanistic Insight into a Sugar‐Accelerated Tin‐Catalyzed Cascade Synthesis of α‐Hydroxy‐γ‐butyrolactone from Formaldehyde

Mechanistic Insight into a Sugar‐Accelerated Tin‐Catalyzed Cascade Synthesis of α‐Hydroxy‐γ‐butyrolactone from Formaldehyde

The Silicate-Mediated Formose Reaction: Bottom-Up Synthesis of Sugar Silicates

Distributions of CHN compounds in meteorites record organic syntheses in the early solar system

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