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Aldolases 2-deoxyribose

An interesting enzyme-catalyzed three-component aldolization reaction has been described by Gijsen and Wong [18]. Here, acetaldeyde, 2-substituted acetaldehydes, and dihydroxyacetone phosphate react in the presence of the aldolases 2-deoxyribose-5-phosphate aldolase (DERA) and fructose 1,6-diphosphate aldolase (RAMA) forming the corresponding 5-deoxyketose derivatives (Scheme 9.9). [Pg.281]

DHAP-dependent aldolases Pyruvate dependent aldolases Deoxyribose 5 -phosphate aldolase —h... [Pg.69]

In contrast to transketolase and the DHAP-dependent aldolases, deoxyribose aldolase (DERA) catalyzes the aldol reaction with the simple aldehyde, acetaldehyde. In vivo it catalyzes the formation of 2-deoxyribose-5-phosphate, the building block of DNA, from acetaldehyde and D-glyceraldehyde-3-phosphate, but in vitro it can catalyze the aldol reaction of acetaldehyde with other non-phosphorylated aldehydes. The example shown in Scheme 6.28 involves a tandem aldol reaction... [Pg.129]

Lyases decarboxylase, dehydratase, deoxyribose-phosphate aldolase nonhydrolytic bond cleavage... [Pg.17]

Aldolases catalyze asymmetric aldol reactions via either Schiff base formation (type I aldolase) or activation by Zn2+ (type II aldolase) (Figure 1.16). The most common natural donors of aldoalses are dihydroxyacetone phosphate (DHAP), pyruvate/phosphoenolpyruvate (PEP), acetaldehyde and glycine (Figure 1.17) [71], When acetaldehyde is used as the donor, 2-deoxyribose-5-phosphate aldolases (DERAs) are able to catalyze a sequential aldol reaction to form 2,4-didexoyhexoses [72,73]. Aldolases have been used to synthesize a variety of carbohydrates and derivatives, such as azasugars, cyclitols and densely functionalized chiral linear or cyclic molecules [74,75]. [Pg.27]

Wong, C.-H. and Greenberg, W.A. (2007) Asymmetric synthesis using deoxyribose-5-phosphate aldolase. [Pg.33]

The cholesterol-lowering drug atorvastatin, marketed as Lipitor, is an example where biocatalysis research has been applied extensively and is in industrial use. The enzyme 2-deoxyribose-5-phosphate aldolase (DERA) has been a target of directed evolution for the production of atorvastatin intermediates [8,9,71]. DeSantis and coworkers [8,9] used structure-based... [Pg.73]

DeSantis, G., Liu, J., Clark, D.R et al. (2003) Structure-based mutagenesis approaches toward expanding the substrate specificity of D-2-deoxyribose-5-phosphate aldolase. Bioorganic and Medicinal Chemistry, 11, 43-52. [Pg.76]

Figure 14.12 Asymmetric tandem aldol reaction using 2-deoxyribose-5-phosphate aldolase (DERA) and its application for production of Atorvastatin... Figure 14.12 Asymmetric tandem aldol reaction using 2-deoxyribose-5-phosphate aldolase (DERA) and its application for production of Atorvastatin...
Gijsen, H.J.M. and Wong, C.-H. (1994) Unprecedented asymmetric aldol reactions with three aldehyde substrates catalyzed by 2-deoxyribose-5-phosphate aldolase. Journal of the American Chemical Society, 116 (18), 8422-8423. [Pg.336]

Deoxy-D-manno-octulosonate aldolase, which facilitates the reaction of pyruvate with D-arabinose to form 3-deoxy-D-manno-octulosonate, an important component of bacterial cell walls. (5) 2-Oxo-4-hydroxyglutar-ate aldolase, which converts 2-oxo-4-hydroxyglutarate to pyruvate and glyoxylate. (6) Deoxyribose-phosphate aldolase, which converts 2-deoxy-D-ribose 5-phosphate... [Pg.46]

DEOXYRIBONUCLEASES 2 -Deoxyribonucleoside diphosphate, RIBONUCLEOTIDE REDUCTASE 2-DEOXYRIBOSE-5-PHOSPHATE ALDOLASE DEOXYTHYMIDINE KINASE DEP,... [Pg.735]

Concerning aldolases, the cloning of enzymes is becoming more and more common. Thus the bacterial fuculose-1-phosphate aldolase (EC 4.1.2.17) and 2-deoxyribose-5-phosphate aldolase (EC 4.1.2.4) have been recently overexpressed in E. coli and their synthetic use has been examined.115,116... [Pg.237]

To expand the substrate specificity and stereoselectivity of the aldolase DERA (2-deoxyribose-5-phosphate aldolase, E.C. 4.1.2.4), both site-specific mutagenesis and random mutagenesis have been investigated (DeSantis, 2003). The goal was to extend substrate specificity to the unnatural non-phosphorylated substrate, D-2-deoxyribose. [Pg.304]

The chiral 2,4-dideoxyhexose derivative required for the HMG CoA reductase inhibitors has also been prepared using 2-deoxyribose-5-phosphate aldolase (DERA).The reactions start with a stereospecific addition of acetaldehyde (44) (Fig. 18.14) to a substituted acetaldehyde to form a 3-hydroxyl-substituted butyraldehyde 45, which reacts subsequently with another acetaldehyde to form a 2,4-dideoxyhexose derivative 46. DERA has been expressed in Escherichia coli (Gijsen and Wong, 1995). [Pg.335]

In a different study, 2-D-deoxyribose-5-phosphate aldolase (DRA) was used in the synthetic direction to synthesize with high stereospecificity a wide range of aldol products169 according to equation 29 for a variety of X and Y substituents. The method proved to be an efficient one for the synthesis of some aza-sugars. [Pg.1298]


See other pages where Aldolases 2-deoxyribose is mentioned: [Pg.272]    [Pg.249]    [Pg.286]    [Pg.287]    [Pg.346]    [Pg.90]    [Pg.594]    [Pg.594]    [Pg.17]    [Pg.128]    [Pg.332]    [Pg.78]    [Pg.419]    [Pg.228]    [Pg.469]    [Pg.700]    [Pg.287]    [Pg.179]    [Pg.346]    [Pg.524]    [Pg.397]    [Pg.413]    [Pg.243]    [Pg.267]    [Pg.270]   


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2-deoxyribose-5-phosphate aldolase

2-deoxyribose-5-phosphate aldolase DERA)

Aldolases deoxyribose-phosphate aldolase

Deoxyribose

Recombinant 2-deoxyribose 5-phosphate aldolase

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