Study on the (R)-oxynitrilase activity of Pouteria sapota

Solı́s, Aida; Luna, Héctor; Manjarrez, Norberto; Pérez, Herminia I.

doi:10.1016/j.tet.2004.07.102

Cited by 21 publications

(11 citation statements)

References 20 publications

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“…The (R)-hydroxynitrilase (HNL) was extracted [45] and assayed [46] according to established references. Naproxen is commercially available and naproxen chloride is prepared according to a procedure developed by Solis et al [37]. Melting points were recorded on an electrothermal melting point apparatus and were uncorrected.…”

Section: Methodsmentioning

confidence: 99%

“…A solution of Naproxen chloride (S)-14 [37] in 10 ml dry methylene chloride was added dropwise by a syringe to a solution of the cyanohydrin (0.01 mol) and pyridine (0.01 mol, 0.85 ml) in 10 ml dry methylene chloride with stirring at 0 °C under dry argon atmosphere. The reaction mixture was stirred for further 3 h at r.t. An additional volume of methylene chloride (30 ml) was added, then the reaction mixture was washed with a saturated solution of sodium carbonate (3 × 20 ml), distilled water (3 × 20 ml) and dried over anhydrous sodium sulfate.…”

Section: Reaction Of Cyanohydrins (Rs)-3 (R)-3 (Rs)-5 and (S)-5 Wmentioning

confidence: 99%

“…The use of (S)-Naproxen ® (13) as a derivatizing agent to determine the optical purity of organic compounds [37] and as a chiral resolving agent for converting racemates to a mixture …”

Section: Chemistrymentioning

confidence: 99%

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Preparation and reactions of optically active cyanohydrins using the (R)-hydroxynitrile lyase from Prunus amygdalus

Yosef

Morsy

Mahran

et al. 2007

JICS

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Cyanuration of 2-naphthaldehyde (1) and 5-methyl-2-furaldehyde (2) yielded the racemic 2-hydroxy-2-(β-naphthyl)ethanenitrile (R,S)-3 and 2-hydroxy-2-(5-methyl-2-furyl)ethanenitrile (R,S)-5, respectively. The same reaction can be completed by using acetone cyanohydrin (4) as a transcyanating agent. The optically active (R)-3 and (S)-5 could be respectively obtained by hydrocyanation of 1 and 2 using (R)-hydroxynitrile lyase (R)-PaHNL [EC 4.1.2.10] from almonds (Prunus amygdalus) as a chiral catalyst. Cyanohydrins 3 and 5 in their racemic and optically active forms undergo a number of transformations which involve either the hydroxyl group or the cyanide function. Moreover, derivatization of 3 and 5 with (S)-Naproxen ® chloride (S)-14 gave the respective diastereoisomers. The optical activity of (R)-3 and (S)-5 as well as their derivatives were recorded. The postulated structures for the new products were supported with compatible elementary and spectroscopic (IR, 1 H NMR, 13 C NMR, MS, and single crystal X-Ray crystallography) analyses. The antimicrobial activity of some selected racemic new products and their respective optically active analogues were also undertaken.

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Section: Methodsmentioning

confidence: 99%

Section: Reaction Of Cyanohydrins (Rs)-3 (R)-3 (Rs)-5 and (S)-5 Wmentioning

confidence: 99%

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Preparation and reactions of optically active cyanohydrins using the (R)-hydroxynitrile lyase from Prunus amygdalus

Yosef

Morsy

Mahran

et al. 2007

JICS

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“…Besides, long chain hydrocarbons, alcohols, acids and esters also are found mainly in species occurring in dry regions, for example, Brazilian savannah (David, 1993;Lopez, 2005;Silva, 2007). In addition, Pouteria species have been evaluated as enzymes sources to be used as synthesis reagent as well as biological activity purposes (Lott & Jackes, 2001;Solis et al, 2004;Hernandez et al, 2006). The mainly compounds isolated from each species are showed at Figure 1 and Table 1.…”

Section: Chemical Composition Of Pouteria Speciesmentioning

confidence: 99%

Genus Pouteria: chemistry and biological activity

Silva¹,

Simeoni²,

Silveira³

2009

Rev. bras. farmacogn.

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RESUMO: "Gênero Pouteria: Química e atividade biológica". O gênero Pouteria pertence à família Sapotaceae e pode ser encontrado em muitos continentes. As plantas desse gênero têm sido utilizadas na construção civil, na alimentação e também na medicina popular. Algumas atividades biológicas são reportadas às espécies desse gênero, tais como, antioxidante, anti-inflamatória, antibacteriana e antifúngica, mas seu real potencial como fonte de novos fármacos ainda é pouco conhecido. Assim, uma revisão sobre a composição química e as atividades biológicas de Pouteria é apresentada, com o intuito de estimular a continuação dos estudos das espécies aqui citadas, e a investigação de outras espécies para as quais não foram encontrados relatos.Unitermos: Pouteria, Sapotaceae, triterpenos, flavonoides, plantas medicinais. ABSTRACT:The genus Pouteria belongs to the family Sapotaceae and can be widely found around the World. These plants have been used as building material, as food, because the eatable fruits, as well as remedies in folk medicine. Some biological activities have been reported to species of this genus such as antioxidant, anti-inflammatory, antibacterial and antifungal. However, the real potential of this genus as source of new drugs or phytomedicines remains unknown. Therefore, a review of the so far known chemical composition and biological activities of this genus is presented to stimulate new studies about the species already reported moreover that species have no reference about chemistry or biological activities could be found until now.

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“…Key words: Prunus; biocatalysis; hydroxynitrile lyase; cyanohydrin Hydroxynitrile lyases (HNLs) have been isolated from a wide variety of plant sources, [1][2][3][4] including the Prunus genus, [5][6][7][8][9] and catalyze the stereoselective addition of HCN to carbonyls to produce optically active cyanohydrins. The importance of cyanohydrins, which has been highlighted in several reviews, 5,6) is that they can be readily converted into compounds with diverse biological activities.…”

mentioning

confidence: 99%