Synthesis of L-β-hydroxyaminoacids using serine hydroxymethyltransferase

Saeed, Ashraf; Young, Douglas W.

doi:10.1016/s0040-4020(01)88770-6

Cited by 66 publications

(23 citation statements)

References 30 publications

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“…The aldol addition of glycine to aldehydes is catalyzed by pyridoxal-5 -phosphatedependent (PLP) lyases such as threonine aldolases (ThrA; EC 4.1.2.5) and serine hydroxymethyl transefrases (SHMTs; EC 2.1.2.1) [16,18,19,[122][123][124][125][126][127][128].…”

Section: Glycine/alanine Aldolasesmentioning

confidence: 99%

“…β-Hydroxy-α-amino acids are an important class of natural products with biological activity on their own and also as constituents of many naturally occurring complex compounds such as antibiotics and immunosupressants [122,126,129,130]. They also constitute excellent intermediates for the synthesis of biologically relevant compounds such as idulonic acid mimetics, for example, (3R,5R)-dihydroxy-l-homoproline [134], immunosuppressive lipid mycestericin D [135], 3,4-dihydroxyprolines [136], (2S,3R)-2-amino-3-hydroxybutyrolactone, precursor of monobactam antibiotics [137], or l-threo-3-[4-(methylthio)phenylserine] precursor of thiamphenicol and florfenicol [132]; and sialyl Lewis x mimetics [138], surveyed in previous reviews (Scheme 8.38) [16,17].…”

Section: Glycine/alanine Aldolasesmentioning

confidence: 99%

See 1 more Smart Citation

Enzyme‐Catalyzed Aldol Additions

Clapés¹,

Joglar²

2013

Modern Methods in Stereoselective Aldol Reactions

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Section: Glycine/alanine Aldolasesmentioning

confidence: 99%

Section: Glycine/alanine Aldolasesmentioning

confidence: 99%

Enzyme‐Catalyzed Aldol Additions

Clapés¹,

Joglar²

2013

Modern Methods in Stereoselective Aldol Reactions

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“…In summary, we could demonstrate that the AlkS/P alkB system is an efficient system for the recombinant production of enzymes, for example, for the serine hydroxymethyltransferase GlyA, that has shown much potential in diastereoselective carbon-carbon bond formation (Kimura et al, 1997;Saeed and Young, 1992). This work was supported by a grant to S. Makart from the ETH.…”

mentioning

confidence: 95%

Characterization of the AlkS/P_alkB‐expression system as an efficient tool for the production of recombinant proteins in Escherichia coli fed‐batch fermentations

Makart

Heinemann

Panke

2006

Biotech & Bioengineering

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The availability of suitable, well-characterized, and robust expression systems remains an essential requirement for successful metabolic engineering and recombinant protein production. We investigated the suitability of the Pseudomonas putida GPo1-derived AlkS/P(alkB) expression system in strictly aqueous cultures. By applying the apolar inducer dicyclopropylketone (DCPK) to express green fluorescent protein (GFP) from this system in Escherichia coli and analyzing the resulting cultures on single-cell level by flow cytometry, we found that this expression system gives rise to a homogeneous population of cells, even though the overall system is expected to have a positive feed-back element in the expression of the regulatory gene alkS. Overexpressing E. coli's serine hydroxymethyltransferase gene glyA, we showed that the system was already fully turned on at inducer concentrations as low as 0.005% (v/v). This allows efficient mass production of recombinant enzymes even though DCPK concentrations decreased from 0.05% to 0.01% over the course of a fully aerated cultivation in aqueous medium. Therefore, we elaborated the optimum induction procedure for production of the biocatalytically promising serine hydroxymethyltransferase and found volumetric and specific productivity to increase with specific growth rate in glucose-limited fed-batch cultures. Acetate excretion as a result of recombinant protein production could be avoided in an optimized fermentation protocol by switching earlier to a linear feed. This protocol resulted in a production of a final cell dry weight (CDW) concentration of 52 g/L, producing recombinant GlyA with a maximum specific activity of 6.3 U/mg total protein.

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“…cited in ref. 4), for example, vancomycin (2). The synthesis of these amino acids is thus of importance, an importance which is increased by their use as intermediates in the synthesis of natural products, for example, p-lactams (5)(6)(7).…”

mentioning

confidence: 99%

“…There has been very limited success in the use of enzymes for the chiral synthesis of P-hydroxy-a-amino acids (4,11,12). However, we have recently isolated (10) a novel aldolase from cultures of Streptomyces amakusaensis (ATCC 23876) that catalyses the conversion of P-hydroxy-a-amino acids (7) into '~u t h o r to whom correspondence may be addressed.…”

mentioning

confidence: 99%