Accumulation of Trans-3-Hydroxy-L-Proline by Seeds and Leaves of the Edible Madagascan Legume Lemuropisum edule H. Perrier

Kite, Geoffrey C.; Plant, Alison C.; Burke, Andrew; Simmonds, Monique J. S.; Blaney, W. M.; Fellows, Linda E.

doi:10.2307/4110329

Kew Bulletin

1995

DOI: 10.2307/4110329

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Accumulation of Trans-3-Hydroxy-L-Proline by Seeds and Leaves of the Edible Madagascan Legume Lemuropisum edule H. Perrier

Geoffrey C. Kite¹,

Alison C. Plant²,

Andrew Burke³

et al.

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Cited by 4 publications

(2 citation statements)

References 17 publications

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“…(2 R ,3 S )-3-Hydroxyproline 5 and its epimer (2 S ,3 S )-3-hydroxyproline 6 ( cis - and trans -3-hydroxyproline, respectively) have been isolated from a wide variety of natural sources, including a dried Mediterranean sponge, hydrolysates of the antibiotic telomycin, and collagen of varied origins , and have also been identified as constituents of other natural products. , Accordingly, these amino acids have inspired significant interest from synthetic chemists, with several enantiospecific and asymmetric syntheses being reported to date, in addition to enzymatic methods for their preparation …”

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confidence: 99%

Asymmetric Syntheses of (2R,3S)-3-Hydroxyproline and (2S,3S)-3-Hydroxyproline

et al. 2018

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Two synthetic routes have been developed for the asymmetric syntheses of (2 R,3 S)- and (2 S,3 S)-3-hydroxyproline. The key synthetic step in each of these strategies is the conversion of protected α,δ-dihydroxy-β-amino esters (either 2,3- anti- or 2,3- syn-configured) into β,δ-dihydroxy-α-amino esters (protected forms thereof), via the intermediacy of the corresponding aziridinium ions. The products of these stereospecific rearrangements were then cyclized and deprotected to afford (2 R,3 S)-3-hydroxyproline and (2 S,3 S)-3-hydroxyproline as single diastereoisomers (>99:1 dr) in >26% overall yield.

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Asymmetric Syntheses of (2R,3S)-3-Hydroxyproline and (2S,3S)-3-Hydroxyproline

et al. 2018

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“…Compound 1 showed potent antifeedant activity against larvae of Spodopptera littoralis and S. litura and cytotoxic activity to human fibroblast cells. 11 In view of the above significance, the syntheses of 3-hydroxyproline and prolinols have gained considerable attention from the synthetic community. Several syntheses of 1 and other isomers with varying levels of success have been reported.…”

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Asymmetric Syntheses of All Stereoisomers of 3-Hydroxyproline; A Constituent of Several Bioactive Compounds

Kumar

Chandrasekhar

2012

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Development of a multi-enzymatic cascade reaction for the synthesis of trans-3-hydroxy-l-proline from l-arginine

Kitatsuji

Yamagata

Kino

2015

Appl Microbiol Biotechnol

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Naturally occurring L-hydroxyproline in its four regio- and stereoisomeric forms has been explored as a possible precursor for pharmaceutical agents, yet the selective synthesis of trans-3-hydroxy-L-proline has not been achieved. Our aim was to develop a novel biocatalytic asymmetric method for the synthesis of trans-3-hydroxy-L-proline. So far, we focused on the rhizobial arginine catabolic pathway: arginase and ornithine cyclodeaminase are involved in L-arginine degradation to L-proline via L-ornithine. We hypothesized that trans-3-hydroxy-L-proline should be synthesized if arginase and ornithine cyclodeaminase act on (2S,3S)-3-hydroxyarginine and (2S,3S)-3-hydroxyornithine, respectively. To test this hypothesis, we cloned the genes of L-arginine 3-hydroxylase, arginase, and ornithine cyclodeaminase and overexpressed them in Escherichia coli, with subsequent enzyme purification. After characterization and optimization of each enzyme, a three-step procedure involving L-arginine 3-hydroxylase, arginase, and ornithine cyclodeaminase (in this order) was performed using L-arginine as a starting substrate. At the second step of the procedure, putative hydroxyornithine was formed quantitatively by arginase from (2S,3S)-3-hydroxyarginine. Nuclear magnetic resonance and chiral high-performance liquid chromatography analyses revealed that the absolute configuration of this compound was (2S,3S)-3-hydroxyornithine. In the last step of the procedure, trans-3-hydroxy-L-proline was synthesized selectively by ornithine cyclodeaminase from (2S,3S)-3-hydroxyornithine. Thus, we successfully developed a novel synthetic route, comprised of three reactions, to convert L-arginine to trans-3-hydroxy-L-proline. The excellent selectivity makes this procedure simpler and more efficient than conventional chemical synthesis.

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Accumulation of Trans-3-Hydroxy-L-Proline by Seeds and Leaves of the Edible Madagascan Legume Lemuropisum edule H. Perrier

Cited by 4 publications

References 17 publications

Asymmetric Syntheses of (2R,3S)-3-Hydroxyproline and (2S,3S)-3-Hydroxyproline

Asymmetric Syntheses of (2R,3S)-3-Hydroxyproline and (2S,3S)-3-Hydroxyproline

Asymmetric Syntheses of All Stereoisomers of 3-Hydroxyproline; A Constituent of Several Bioactive Compounds

Development of a multi-enzymatic cascade reaction for the synthesis of trans-3-hydroxy-l-proline from l-arginine

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