A New Synthesis of Threonine

Sato, Mikio; Okawa, Kenji; Akabori, Shirô

doi:10.1246/bcsj.30.937

Cited by 95 publications

(15 citation statements)

References 4 publications

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“…As with serine, threonine and allothreonine decompose by #-elimination, dealdolization and decarboxylation. The synthesis of threonine from the reaction Glycine + Acetaldehyde ~ Threonine + Allothreonine would be expected, although it has not been investigated except using Cu +2 and pyridoxal as a catalyst (Sato et al 1957;Metzler et al 1954). This reaction would probably be less favorable than the serine synthesis, so threonine would have been considerably less abundant than serine in the primitive ocean.…”

Section: Glycine + H2co ~-Serinementioning

confidence: 99%

Reasons for the occurrence of the twenty coded protein amino acids

1981

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Factors involved in the selection of the 20 protein L-alpha-amino acids during chemical evolution and the early stages of Darwinian evolution are discussed. The selection is considered on the basis of the availability in the primitive ocean, function in proteins, the stability of the amino acid and its peptides, stability to racemization, and stability on the transfer RNA. We conclude that aspartic acid, glutamic acid, arginine, lysine, serine and possibly threonine are the best choices for acidic, basic and hydroxy amino acids. The hydrophobic amino acids are reasonable choices, except for the puzzling absences of alpha-amino-n-butyric acid, norvaline and norleucine. The choices of the sulfur and aromatic amino acids seem reasonable, but are not compelling. Asparagine and glutamine are apparently not primitive. If life were to arise on another planet, we would expect that the catalysts would be poly-alpha-amino acids and that about 75% of the amino acids would be the same as on the earth.

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Section: Glycine + H2co ~-Serinementioning

confidence: 99%

Reasons for the occurrence of the twenty coded protein amino acids

1981

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“…The reaction of the copper ( II )-glycine complex with ke tones or aldehydes produces ^-hydroxyamino acids (Equation 27) (1, 65).…”

Section: ^Jl-chmentioning

confidence: 99%

Reactions of Ligands in Metal Complexes

Busch¹

1962

Advances in Chemistry

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“…Under alkaline conditions, the formed carbanion would serve as a nucleophile that can condense with a carbonyl moiety such as formaldehyde or acetaldehyde. 1,4 However, it was later proposed that the amino acid metal complexes first undergo Schiff base formation with the aldehyde followed by the subsequent activation of the α-carbon to generate carbanion. 3,7 The formation of the Schiff base adducts was assumed to enhance even more the acidity of the α-carbon, allowing the reaction to proceed at milder pH conditions and with higher yields.…”

Section: ■ Introductionmentioning

confidence: 99%

De Novo Synthesis of Amino Acids during the Maillard Reaction: qTOF/ESI Mass Spectrometric Evidence for the Mechanism of Akabori Transformation

Nashalian

Yaylayan

2014

J. Agric. Food Chem.

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The transformation of α-amino acids into their hydroxymethyl derivatives during the Maillard reaction is an intriguing possibility for catalysis by metal salts in the presence of Strecker aldehydes; the process is commonly known as the Akabori reaction. The mechanism of this reaction was studied in the presence of glucose, using glycine copper complex and paraformaldehyde as Akabori model system in aqueous mixtures heated at 110 °C for 2 h and subsequently analyzed by qTOF/ESI/MS. Isotope-labeling studies of the various products identified have provided for the first time mass spectrometric evidence for the detailed mechanism of Akabori transformation, particularly the formation of Schiff base adducts prior to the final conversion into serine and hydroxymethyl-serine. Furthermore, the results have indicated that sugars do not interfere with such transformations and, on the contrary, the presence of glycine–copper complexes in the Maillard model systems can enhance the production of Maillard reaction intermediates.

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A New Synthesis of Threonine

Abstract: A new method is described for the synthesis of threonine from acetaldehyde and copper glycinate. This method gives a mixture of allo-threonine and threonine in a high yield (64%).

Cited by 95 publications

References 4 publications

Reasons for the occurrence of the twenty coded protein amino acids

Reasons for the occurrence of the twenty coded protein amino acids

Reactions of Ligands in Metal Complexes

De Novo Synthesis of Amino Acids during the Maillard Reaction: qTOF/ESI Mass Spectrometric Evidence for the Mechanism of Akabori Transformation

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