An asymmetric synthesis of l‐[2‐13C]aspartic acid from sodium [2‐13C]acetate

Takatori, Kazuhiko; Nishihara, Mikiko; Kajiwara, Masahiro

doi:10.1002/(sici)1099-1344(199907)42:7<701::aid-jlcr232>3.3.co;2-a

Cited by 4 publications

(4 citation statements)

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“…Therefore we prepared mono-( 8) 32 and di-phenyl ( 7) [33][34] allylmorpholin-2-ones in both enantiomeric forms in just 4 steps, as two new chiral platforms containing a homoallylic amine. Following the rationale presented in Scheme 1 (2), the phenyl substituents were chosen as these would both facilitate rapid removal of part of the chiral platform post Prins cyclisation and crucially block one face from anion trapping.…”

Section: Resultsmentioning

confidence: 99%

A Stereoselective aza-Prins Reaction: Rapid Access to Enantiopure Piperidines and Pipecolic Acids

et al. 2021

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The aza-Prins reaction is a widely employed and highly efficient method for the preparation of saturated nitrogencontaining heterocycles. Its major drawback has always been a lack of diastereoselectivity and the formation of racemic products. Herein we address these problems and report, for the first time, the synthesis of both diastereomerically and enantiopure multiplysubstituted piperidines via the aza-Prins reaction. This method will be widely applicable for natural product synthesis and is exemplified here by the synthesis of enantiopure pipecolic acid derivatives.

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Section: Resultsmentioning

confidence: 99%

A Stereoselective aza-Prins Reaction: Rapid Access to Enantiopure Piperidines and Pipecolic Acids

et al. 2021

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“…Using oxazines, in particular the Williams oxazines supersedes some of these issues as the oxazine ring is cleaved under hydrogenation conditions and the isotopically labeled amino acid is isolated by ion-exchange chromatography. Oxazines have been used extensively for the synthesis of labeled amino acids including aspartic acid, glutamic acid, phenylalanine, tyrosine, lysine, glycine as well as alanine [71][72][73][74][75][76][77]. For example, Williams and coworkers prepared (5S,6R)-½2; 3-13 C 2 ; 15 N4-benzyloxy-5,6-diphenyl-2,3,5,6-tetrahydro-4H-oxazine-2-one 484j 11 Synthesis of Isotopically Labeled a-Amino Acids 59 from benzoin 58 using a lipase-mediated kinetic resolution as the key step (Scheme 11.16) [77].…”

Section: Chemical Asymmetric Methodsmentioning

confidence: 99%

Synthesis of Isotopically Labeled α‐Amino Acids

Reid

Sutherland

2009

Amino Acids, Peptides and Proteins in Organic Chemistry

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“…l ‐[2‐ 13 C]Aspartic acid, which is not commercially available, was synthesized from sodium acetate (99 atom. % 13 C; Cambridge Isotope Laboratories, Andover, MA, USA) by our method [12]. [2‐ 13 C]Glycine (99 atom.…”

Section: Methodsmentioning

confidence: 99%

Metabolic pathways leading from amino acids to vitamin B₁₂ in Propionibacterium shermanii, and the sources of the seven methyl carbons

Iida

Kajiwara

2007

The FEBS Journal

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The metabolic pathways leading from l‐[2‐13C]aspartic acid, [2‐13C]glycine and l‐[methyl‐13C]methionine to vitamin B12 were investigated, focusing on the biosynthetic pathways leading to the aminopropanol moiety of vitamin B12 and on the role of the Shemin pathway leading to δ‐aminolevulinic acid (a biosynthetic intermediate of tetrapyrrole), by means of feeding experiments with Propionibacterium shermanii in combination with 13C‐NMR spectroscopy. The 13C‐methylene carbons of l‐[2‐13C]aspartic acid, which is transformed to [2‐13C]glycine via l‐[2‐13C]threonine, and [2‐13C]glycine added to the culture medium served mainly to enrich the seven methyl carbons of the corrin ring through C‐methylation by S‐adenosyl‐l‐[methyl‐13C]methionine derived from catabolically generated l‐[methyl‐13C]methionine in the presence of tetrahydrofolic acid. The results indicate that the catabolism of these amino acids predominates over pathways leading to (2R)‐1‐amino‐2‐propanol or δ‐aminolevulinic acid in P. shermanii. Feeding of l‐[methyl‐13C]methionine efficiently enriched all seven methyl carbons. In the cases of [2‐13C]glycine and l‐[methyl‐13C]methionine, the 13C‐enrichment ratio of the methyl carbon at C‐25 (the site of the first C‐methylation) was less than those of the other six methyl carbons, probably due to the influence of endogenous d‐glucose in P. shermanii. The almost identical 13C‐enrichment ratios of the other six methyl carbons indicated that these C‐methylations during vitamin B12 biosynthesis were completed before the amino acids were completely consumed. However, in the case of l‐[2‐13C]aspartic acid, the 13C‐enrichment ratios of five methyl carbons were low and similar, whereas the last two sites of C‐methylation (C‐53 and C‐35) were not labeled, presumably because of complete consumption of the smaller amount of added label. The ratios of 13C‐incorporation into the seven methyl carbons are influenced by the conditions of amino acid feeding experiments in a manner that is dependent upon the order of C‐methylation in the corrin ring of vitamin B12.

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An asymmetric synthesis of l‐[2‐13C]aspartic acid from sodium [2‐13C]acetate

Cited by 4 publications

References 0 publications

A Stereoselective aza-Prins Reaction: Rapid Access to Enantiopure Piperidines and Pipecolic Acids

A Stereoselective aza-Prins Reaction: Rapid Access to Enantiopure Piperidines and Pipecolic Acids

Synthesis of Isotopically Labeled α‐Amino Acids

Metabolic pathways leading from amino acids to vitamin B₁₂ in Propionibacterium shermanii, and the sources of the seven methyl carbons

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An asymmetric synthesis of l‐[2‐13C]aspartic acid from sodium [2‐13C]acetate

Cited by 4 publications

References 0 publications

A Stereoselective aza-Prins Reaction: Rapid Access to Enantiopure Piperidines and Pipecolic Acids

A Stereoselective aza-Prins Reaction: Rapid Access to Enantiopure Piperidines and Pipecolic Acids

Synthesis of Isotopically Labeled α‐Amino Acids

Metabolic pathways leading from amino acids to vitamin B12 in Propionibacterium shermanii, and the sources of the seven methyl carbons

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Product

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Metabolic pathways leading from amino acids to vitamin B₁₂ in Propionibacterium shermanii, and the sources of the seven methyl carbons