Synthesis of the constrained glutamate analogues (2S,1′R,2′R)- and (2S,1′S,2′S)-2-(2′-carboxycyclobutyl)glycines L-CBG-II and L-CBG-I by enzymatic transamination

Gu, Xin; Xian, Mo; Roy-Faure, Sophie; Bolte, Jean; Aitken, David J.; Gefflaut, Thierry

doi:10.1016/j.tetlet.2005.10.156

Cited by 32 publications

(23 citation statements)

References 37 publications

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“…Optically pure trans-cyclobutane analogs (178) and (179) of glutamic acid were prepared by highly selective enzymic transamination of racemic trans-(2-carboxy-cyclobutyl)oxoacetate, which was synthesized in five steps from maleic anhydride [252]. (2S,1 0 R,2 0 R) and (2S,1 0 S,2 0 S)-2-(2 0 -carboxycyclobutyl)glycines L-CBG-II and L-CBG-I were obtained using aspartate aminotransferase and branched-chain aminotransferase, respectively.…”

Section: Synthetic Analogs Of Natural Alkaloids With Cyclobutane Ringmentioning

confidence: 99%

Bioactive cyclobutane-containing alkaloids

2007

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The present review describes research on novel natural cyclobutane-containing alkaloids and synthetic compounds isolated from terrestrial and marine species. More than 210 compounds have been confirmed to show antimicrobial, antibacterial, anticancer, and other activities. Structures, origins, biosynthesis, photodimerization, and biological activities of a selection of cyclobutane-containing alkaloids and selected synthetic analogs of natural alkaloids are reviewed.

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Section: Synthetic Analogs Of Natural Alkaloids With Cyclobutane Ringmentioning

confidence: 99%

Bioactive cyclobutane-containing alkaloids

2007

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“…In this case the amino acid racemase is of course omitted [Scheme 14 (b)]. [67][68][69] Interestingly, amino acid dehydrogenases and atransaminases have also been coupled in a linear way, realizing a system for deracemization of amino acids. [70] Branched-chain amino acid transaminase (BCAAT) from Sinorhizobium meliloti ATCC 51124 was cloned and overexpressed in E. coli.…”

Section: Multi-enzymatic Synthesis Of Amines and Amino Acids Employinmentioning

confidence: 99%

“…Since amino acid transaminases are usually less substrate‐specific than AADHs, an analogous methodology has been applied for the preparation of L ‐amino acids which could not be produced by direct enzymatic reductive amination, e.g., β‐ and γ‐branched glutamic acid derivatives. In this case the amino acid racemase is of course omitted [Scheme ( b )] 67–69…”

Section: Multi‐enzyme Cascade Processesmentioning

confidence: 99%

Multi‐Enzymatic Cascade Reactions: Overview and Perspectives

Brucher²,

2011

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Multi-enzymatic cascade reactions, i.e., the combination of several enzymatic transformations in concurrent one-pot processes, offer considerable advantages: the demand of time, costs and chemicals for product recovery may be reduced, reversible reactions can be driven to completion and the concentration of harmful or unstable compounds can be kept to a minimum. This review summarizes the developments in multi-enzymatic cascades employed for the asymmetric synthesis of chiral alcohols, amines and amino acids, as well as for C À C bond formation. In addition, a general classification of biocatalytic cascade systems is provided and bioprocess engineering aspects associated with the topic are discussed.

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“…Cofactor regeneration for the AADH is supplied by formate dehydrogenase [29] ( Figure 2D). An analogous methodology has been developed, omitting the amino acid racemase, for the preparation of L-amino acids which could not be produced by direct enzymatic reductive amination as β-and γ-branched glutamic acid derivatives [30]. Furthermore, α-AT and AADH have also been coupled in an amino acid deracemization system by Caligiuri et al [31].…”

Section: Multi-enzymatic Synthesis Of Amines and Amino Acids Employinmentioning

confidence: 99%

Enzyme catalysed tandem reactions

Oroz‐Guinea

García‐Junceda

2013

Current Opinion in Chemical Biology

129

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To transfer to the laboratory, the excellent efficiency shown by enzymes in Nature, biocatalysis, had to mimic several synthetic strategies used by the living organisms. Biosynthetic pathways are examples of tandem catalysis and may be assimilated in the biocatalysis field for the use of isolated multi-enzyme systems in the homogeneous phase. The concurrent action of several enzymes that work sequentially presents extraordinary advantages from the synthetic point of view, since it permits a reversible process to become irreversible, to shift the equilibrium reaction in such a way that enantiopure compounds can be obtained from prochiral or racemic substrates, reduce or eliminate problems due to product inhibition or prevent the shortage of substrates by dilution or degradation in the bulk media, etc. In this review we want to illustrate the developments of recent studies involving in vitro multi-enzyme reactions for the synthesis of different classes of organic compounds.

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Synthesis of the constrained glutamate analogues (2S,1′R,2′R)- and (2S,1′S,2′S)-2-(2′-carboxycyclobutyl)glycines L-CBG-II and L-CBG-I by enzymatic transamination

Cited by 32 publications

References 37 publications

Bioactive cyclobutane-containing alkaloids

Bioactive cyclobutane-containing alkaloids

Multi‐Enzymatic Cascade Reactions: Overview and Perspectives

Enzyme catalysed tandem reactions

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