Convenient green preparation of dipeptides using unprotected α-amino acids

Ezawa, Tetsuya; Jung, Seunghee; Kawashima, Yuya; Noguchi, Takuya; Imai, Nobuyuki

doi:10.1016/j.tetasy.2016.11.009

Cited by 8 publications

(3 citation statements)

References 21 publications

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“…The different amino acid amides and p-nitroanilide derivatives used for activity measurement of PsyPAH were purchased from VWR (VWR International Eurolab S.L, Barcelona, Spain), TCI chemicals, Alfa Aesar, or Acros (Cymit Quimica, Barcelona, Spain). Other amino acid amides were synthesized as previously described [19] (see supporting information). Other chemicals were from Sigma Aldrich (Sigma-Aldrich, St. Louis, MO, USA).…”

Section: Methodsmentioning

confidence: 99%

A New L-Proline Amide Hydrolase with Potential Application within the Amidase Process

et al. 2021

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L-proline amide hydrolase (PAH, EC 3.5.1.101) is a barely described enzyme belonging to the peptidase S33 family, and is highly similar to prolyl aminopeptidases (PAP, EC. 3.4.11.5). Besides being an S-stereoselective character towards piperidine-based carboxamides, this enzyme also hydrolyses different L-amino acid amides, turning it into a potential biocatalyst within the Amidase Process. In this work, we report the characterization of L-proline amide hydrolase from Pseudomonas syringae (PsyPAH) together with the first X-ray structure for this class of L-amino acid amidases. Recombinant PsyPAH showed optimal conditions at pH 7.0 and 35 °C, with an apparent thermal melting temperature of 46 °C. The enzyme behaved as a monomer at the optimal pH. The L-enantioselective hydrolytic activity towards different canonical and non-canonical amino-acid amides was confirmed. Structural analysis suggests key residues in the enzymatic activity.

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Section: Methodsmentioning

confidence: 99%

A New L-Proline Amide Hydrolase with Potential Application within the Amidase Process

et al. 2021

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“…20 After saponification of the ethyl ester 14 with lithium hydroxide, the corresponding carboxylic acid 15 was coupled with (2S,3S)-βMePhe to give carboxylic acid (14S,15S)-16 in 71% yield. 21 TBS deprotection of the carboxylic acid provided carboxylic acid (14S,15S)-17 in 75% yield. Carboxylic acid (14R,15R)-17 was prepared from carboxylic acid 15 using (2R,3R)-βMePhe in 62% yield over two steps.…”

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confidence: 99%

“…Subsequent conversion of the nitrile 13 to the aldehyde, followed by the Horner–Wadsworth–Emmons reaction, gave the unsaturated ester 14 in 87% yield in two steps . After saponification of the ethyl ester 14 with lithium hydroxide, the corresponding carboxylic acid 15 was coupled with (2 S ,3 S )-βMePhe to give carboxylic acid (14 S ,15 S )- 16 in 71% yield . TBS deprotection of the carboxylic acid provided carboxylic acid (14 S ,15 S )- 17 in 75% yield.…”

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confidence: 99%

Micromonosporamide A with Glutamine-Dependent Cytotoxicity from Micromonospora sp. MM609M-173N6: Isolation, Stereochemical Determination, and Synthesis

et al. 2021

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An acyldipeptide, micromonosporamide A, was isolated from the fermentation broth of Micromonospora sp. MM609M-173N6 by bioassay-guided fractionation using a glutamine compensation assay. The planar structure was elucidated on the basis of comprehensive one-and two-dimensional nuclear magnetic resonance and high-resolution mass spectrometry. The relative and absolute configuration of the entire molecule were determined using a combined approach, involving chromatographic analysis by liquid chromatography−mass spectrometry, advanced Marfey's method, and total synthesis. Micromonosporamide A exhibited glutamine-dependent antiproliferative activity.

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Mechanochemical processes with the reaction-induced mechanical activation. Chemo-mechanochemical effect

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2018

Russ Chem Bull

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Convenient green preparation of dipeptides using unprotected α-amino acids

Cited by 8 publications

References 21 publications

A New L-Proline Amide Hydrolase with Potential Application within the Amidase Process

A New L-Proline Amide Hydrolase with Potential Application within the Amidase Process

Micromonosporamide A with Glutamine-Dependent Cytotoxicity from Micromonospora sp. MM609M-173N6: Isolation, Stereochemical Determination, and Synthesis

Mechanochemical processes with the reaction-induced mechanical activation. Chemo-mechanochemical effect

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