Serine hydroxymethyl transferase from Streptococcus thermophilus and L-threonine aldolase from Escherichia coli as stereocomplementary biocatalysts for the synthesis of β-hydroxy-α,ω-diamino acid derivatives

Mariana L. Gutierrez, Xavier Garrabou, Eleonora Agosta, Stefano Servi, Teodor Parella, Jesús Joglar, Pere Clapés

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    Abstract

    A novel serine hydroxymethyl transferase from Streptococcus thermophilus (SHMT) and a L-threonine aldolase from Escherichia coli (LTA) were used as stereocomplementary biocatalysts for the aldol addition of glycine to N-Cbz amino aldehydes and benzyloxyacetaldehyde (Cbz = benzyloxycarbonyl). Both threonine aldolases were classified as low-specific L-allo-threonine aldolases, and by manipulating reaction parameters, such as temperature, glycine concentration, and reaction media, SHMT yielded exclusively L-erythro diastereomers in 34-60% conversion, whereas LTA gave L-threo diastereomers in 30:70 to 16:84 diastereomeric ratios and with 40-68% conversion to product. SHMT is among the most stereoselective L-threonine aldolases described. This is due, among other things, to its activity-temperature dependence: at 4°C SHMT has high synthetic activity but negligible retroaldol activity on L-threonine. Thus, the kinetic L-erythro isomer was largely favored and the reactions were virtually irreversible, highly stereoselective, and in turn, gave excellent conversion. It was also found that treatment of the prepared N-Cbz-γ-amino-β-hydroxy-αamino acid derivatives with potassium hydroxide (1M) resulted in the spontaneous formation of 2-oxazolidinone derivatives of the β-hydroxyl and γ-amino groups in quantitative yield. This reaction might be useful for further chemical manipulations of the products. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.
    Original languageEnglish
    Pages (from-to)4647-4656
    JournalChemistry - A European Journal
    Volume14
    Issue number15
    DOIs
    Publication statusPublished - 19 May 2008

    Keywords

    • Aldol reaction
    • Aldolases
    • Asymmetric synthesis
    • Biotransformations
    • Lyases

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