Synthesis of Pyranoid Sugar &amp;#945;-Amino Acid Derivatives from 2-Oxo-Dgluconic Acid

Schmidt, Stephan; Teich, Lars; Khodja, Mohamed; Sicker, Dieter

doi:10.2174/1570178053202946

Cited by 2 publications

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“…Sugar amino acids (SAAs) are pyranoid or furanoid containing amino and carboxyl groups. − In recent decades, α-SAAs, β-SAAs, − γ-SAAs, δ-SAAs, − and alkylated-SAAs have been investigated widely on synthesis, conformation, secondary structures of their homooligomers, and biological activities. Especially, cyclic SAAs attract much attention in terms of biological activities and host−guest chemistry on the basis of their pyranose or furanose rings. − Since cyclic SAAs belong to the category of cyclic peptides, which have been shown as useful building blocks for molecular assembly, it is interesting to explore the ability of cyclic SAAs for the molecular architecture with biological activities or functions.…”

Section: Introductionmentioning

confidence: 99%

“…Sugar amino acids (SAAs) are pyranoid or furanoid containing amino and carboxyl groups. [1][2][3][4][5][6][7] In recent decades, R-SAAs, 8 β-SAAs, [9][10][11] γ-SAAs, 12 δ-SAAs, [13][14][15][16] and alkylated-SAAs 17 have been investigated widely on synthesis, conformation, secondary structures of their homooligomers, and biological activities. Especially, cyclic SAAs attract much attention in terms of biological activities and host-guest chemistry on the basis of their pyranose or furanose rings.…”

Section: Introductionmentioning

confidence: 99%

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Columnar Assembly of Cyclic β-Amino Acid Functionalized with Pyranose Rings

Fujimura¹,

Hirata²,

Morita³

et al. 2006

Biomacromolecules

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A novel cyclic trimer and tetramer of protected beta-glycamino acids were synthesized and investigated on conformation and assembly formation. A characteristic point of these cyclic beta-glycamino acids is their better solubility than other cyclic beta-amino acids due to the pyranose rings. Thus, the assembling process of the cyclic molecules could be examined by CD or NMR spectroscopy. FT-IR and NMR measurements and geometry optimization revealed a highly symmetric and planar conformation for each cyclic beta-peptide with all-trans amide groups. The amide groups in the cyclic peptides took a vertical orientation against the cyclic skeleton to be suitably arranged for intermolecular hydrogen bonds, which should promote formation of molecular assembly in a columnar structure through molecular stacking. These cyclic beta-peptides were successfully crystallized to yield rod-shaped molecular assemblies in nanometer sizes. Evidence for the columnar structure in the crystals was obtained by electron diffraction analysis, which showed a layer spacing of ca. 4.8 A. Interestingly, the molecular assembly of the cyclic trimer showed a high aspect ratio, width less than 40 nm, and length more than 2 mum, suggesting stable molecular stacking in the column.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Columnar Assembly of Cyclic β-Amino Acid Functionalized with Pyranose Rings

Fujimura¹,

Hirata²,

Morita³

et al. 2006

Biomacromolecules

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Microbiologically Produced Carboxylic Acids Used as Building Blocks in Organic Synthesis

Aurich

Specht

Müller

et al. 2012

Subcellular Biochemistry

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Oxo- and hydroxy-carboxylic acids are of special interest in organic synthesis. However, their introduction by chemical reactions tends to be troublesome especially with regard to stereoselectivity. We describe herein the biotechnological preparation of selected oxo- and hydroxycarboxylic acids under "green" conditions and their use as promising new building blocks. Thereby, our biotechnological goal was the development of process fundamentals regarding the variable use of renewable raw materials, the development of a multi purpose bioreactor and application of a pilot plant with standard equipment for organic acid production to minimize the technological effort. Furthermore the development of new product isolation procedures, with the aim of direct product recovery, capture of products or single step operation, was necessary. The application of robust and approved microorganisms, also genetically modified, capable of using a wide range of substrates as well as producing a large spectrum of products, was of special importance. Microbiologically produced acids, like 2-oxo-glutaric acid and 2-oxo-D-gluconic acid, are useful educts for the chemical synthesis of hydrophilic triazines, spiro-connected heterocycles, benzotriazines, and pyranoic amino acids. The chiral intermediate of the tricarboxylic acid cycle, (2R,3S)-isocitric acid, is another promising compound. For the first time our process provides large quantities of enantiopure trimethyl (2R,3S)-isocitrate which was used in subsequent chemical transformations to provide new chiral entities for further usage in total synthesis and pharmaceutical research.Oxo- and hydroxy-carboxylic acids are of special interest in organic synthesis. However, their introduction by chemical reactions tends to be troublesome especially with regard to stereoselectivity. We describe herein the biotechnological preparation of selected oxo- and hydroxycarboxylic acids under "green" conditions and their use as promising new building blocks. Thereby, our biotechnological goal was the development of process fundamentals regarding the variable use of renewable raw materials, the development of a multi purpose bioreactor and application of a pilot plant with standard equipment for organic acid production to minimize the technological effort. Furthermore the development of new product isolation procedures, with the aim of direct product recovery, capture of products or single step operation, was necessary. The application of robust and approved microorganisms, also genetically modified, capable of using a wide range of substrates as well as producing a large spectrum of products, was of special importance. Microbiologically produced acids, like 2-oxo-glutaric acid and 2-oxo-D-gluconic acid, are useful educts for the chemical synthesis of hydrophilic triazines, spiro-connected heterocycles, benzotriazines, and pyranoic amino acids. The chiral intermediate of the tricarboxylic acid cycle, (2R,3S)-isocitric acid, is another promising compound. For the first time our process provides large qua...

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Synthesis of Pyranoid Sugar α-Amino Acid Derivatives from 2-Oxo-Dgluconic Acid

Cited by 2 publications

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Columnar Assembly of Cyclic β-Amino Acid Functionalized with Pyranose Rings

Columnar Assembly of Cyclic β-Amino Acid Functionalized with Pyranose Rings

Microbiologically Produced Carboxylic Acids Used as Building Blocks in Organic Synthesis

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