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Ashot Vorobyov
Ashot Vorobyov

Hexose


Hexoses are extremely important in biochemistry, both as isolated molecules (such as glucose and fructose) and as building blocks of other compounds such as starch, cellulose, and glycosides. Hexoses can form dihexose (like sucrose) by a condensation reaction that makes 1,6-glycosidic bond.




hexose


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In the linear form, there are 16 aldohexoses and eight 2-ketohexoses, stereoisomers that differ in the spatial position of the hydroxyl groups. These species occur in pairs of optical isomers. Each pair has a conventional name (like "glucose" or "fructose"), and the two members are labeled "D-" or "L-", depending on whether the hydroxyl in position 5, in the Fischer projection of the molecule, is to the right or to the left of the axis, respectively. These labels are independent of the optical activity of the isomers. In general, only one of the two enantiomers occurs naturally (for example, D-glucose) and can be metabolized by animals or fermented by yeasts.


The term "hexose" sometimes is assumed to include deoxyhexoses, such as fucose and rhamnose: compounds with general formula C6H12O6-y that can be described as derived from hexoses by replacement of one or more hydroxyl groups with hydrogen atoms.


In linear form, an aldohexose has four chiral centres, which give 16 possible aldohexose stereoisomers (24),comprising 8 pairs of enantiomers. The linear forms of the eight D-aldohexoses, in the Fischer projection, are


When drawn in this order, the Fischer projections of the D-aldohexoses can be identified with the 3-digit binary numbers from 0 to 7, namely 000, 001, 010, 011, 100, 101, 110, 111. The three bits, from left to right, indicate the position of the hydroxyls on carbons 4, 3, and 2, respectively: to the right if the bit value is 0, and to the left if the value is 1.


In 1897, an unfermentable product obtained by treatment of fructose with bases, in particular lead(II) hydroxide, was given the name glutose, a portmanteau of glucose and fructose, and was claimed to be a 3-ketohexose.[12][13] However, subsequent studies showed that the substance was a mixture of various other compounds.[13][14]


Like most monosaccharides with five or more carbons, each aldohexose or 2-ketohexose also exists in one or more cyclic (closed-chain) forms, derived from the open-chain form by an internal rearrangement between the carbonyl group and one of the hydroxyl groups.


If the sugar is an aldohexose, with the carbonyl in position 1, the reaction may involve the hydroxyl on carbon 4 or carbon 5, creating a hemiacetal with five- or six-membered ring, respectively. If the sugar is a 2-ketohexose, it can only involve the hydroxyl in carbon 5, and will create a hemiketal with a five-membered ring.


The closure turns the carboxyl carbon into a chiral center, which may have either of two configurations, depending on the position of the new hydroxyl. Therefore, each hexose in linear form can produce two distinct closed forms, identified by prefixes "α" and "β".


It has been known since 1926 that hexoses in the crystalline solid state assume the cyclic form. The "α" and "β" forms, which are not enantiomers, will usually crystallize separately as distinct species. For example, D-glucose forms an α crystal that has specific rotation of +112 and melting point of 146 C, as well as a β crystal that has specific rotation of +19 and melting point of 150 C.[4]


Although all hexoses have similar structures and share some general properties, each enantiomer pair has its own chemistry. Fructose is soluble in water, alcohol, and ether.[9] The two enantiomers of each pair generally have vastly different biological properties.


D-Sorbose is commonly used in the commercial synthesis of ascorbic acid.[10] D-Tagatose is a rare natural ketohexose that is found in small quantities in food.[11] D-Fructose is responsible for the sweet taste of many fruits, and is a building block of sucrose, the common sugar.


Hepatic hexose transport was characterized using 3-O-methyl-D-glucose, which is not metabolized by the liver. The kinetic parameters determined in the starved state were taken as basal values for the transport system which showed saturation kinetics with high Vmax and Km values of 161 nmol/mg dry wt./rnin and 39 mM respectively. In the fed state, the Vmax was found to be increased nearly two-fold; this may be due to a phenomenon known as trans-stirnulation. The effects of N2-induced anoxia and of KCN were investigated. In the fasted state, anoxia caused the transport characteristics Vmax and Km to decrease nearly two-fold whereas KCN had the opposite effect as the Vmax and Km were increased by three- and two-fold respectively. In the fed state, anoxia and KCN caused a marked decrease in the transport characteristics.


In the fleshy fruit of cucumbers (Cucumis sativus L.), the phloem flow is unloaded via an apoplasmic pathway, which requires protein carriers to export sugars derived from stachyose and raffinose into the apoplasm. However, transporter(s) involved in this process remain unidentified. Here, we report that a hexose transporter, CsSWEET7a (Sugar Will Eventually be Exported Transporter 7a), was highly expressed in cucumber sink tissues and localized to the plasma membrane in companion cells of the phloem. Its expression level increased gradually during fruit development. Down-regulation of CsSWEET7a by RNA interference (RNAi) resulted in smaller fruit size along with reduced soluble sugar levels and reduced allocation of 14C-labelled carbon to sink tissues. CsSWEET7a overexpression lines showed an opposite phenotype. Interestingly, genes encoding alkaline a-galactosidase (AGA) and sucrose synthase (SUS) were also differentially regulated in CsSWEET7a transgenic lines. Immunohistochemical analysis demonstrated that CsAGA2 co-localized with CsSWEET7a in companion cells, indicating cooperation between AGA and CsSWEET7a in fruit phloem unloading. Our findings indicated that CsSWEET7a is involved in sugar phloem unloading in cucumber fruit by removing hexoses from companion cells to the apoplasmic space to stimulate the raffinose family of oligosaccharides (RFOs) metabolism so that additional sugars can be unloaded to promote fruit growth. This study also provides a possible avenue towards improving fruit production in cucumber.


N2 - In the fleshy fruit of cucumbers (Cucumis sativus L.), the phloem flow is unloaded via an apoplasmic pathway, which requires protein carriers to export sugars derived from stachyose and raffinose into the apoplasm. However, transporter(s) involved in this process remain unidentified. Here, we report that a hexose transporter, CsSWEET7a (Sugar Will Eventually be Exported Transporter 7a), was highly expressed in cucumber sink tissues and localized to the plasma membrane in companion cells of the phloem. Its expression level increased gradually during fruit development. Down-regulation of CsSWEET7a by RNA interference (RNAi) resulted in smaller fruit size along with reduced soluble sugar levels and reduced allocation of 14C-labelled carbon to sink tissues. CsSWEET7a overexpression lines showed an opposite phenotype. Interestingly, genes encoding alkaline a-galactosidase (AGA) and sucrose synthase (SUS) were also differentially regulated in CsSWEET7a transgenic lines. Immunohistochemical analysis demonstrated that CsAGA2 co-localized with CsSWEET7a in companion cells, indicating cooperation between AGA and CsSWEET7a in fruit phloem unloading. Our findings indicated that CsSWEET7a is involved in sugar phloem unloading in cucumber fruit by removing hexoses from companion cells to the apoplasmic space to stimulate the raffinose family of oligosaccharides (RFOs) metabolism so that additional sugars can be unloaded to promote fruit growth. This study also provides a possible avenue towards improving fruit production in cucumber.


AB - In the fleshy fruit of cucumbers (Cucumis sativus L.), the phloem flow is unloaded via an apoplasmic pathway, which requires protein carriers to export sugars derived from stachyose and raffinose into the apoplasm. However, transporter(s) involved in this process remain unidentified. Here, we report that a hexose transporter, CsSWEET7a (Sugar Will Eventually be Exported Transporter 7a), was highly expressed in cucumber sink tissues and localized to the plasma membrane in companion cells of the phloem. Its expression level increased gradually during fruit development. Down-regulation of CsSWEET7a by RNA interference (RNAi) resulted in smaller fruit size along with reduced soluble sugar levels and reduced allocation of 14C-labelled carbon to sink tissues. CsSWEET7a overexpression lines showed an opposite phenotype. Interestingly, genes encoding alkaline a-galactosidase (AGA) and sucrose synthase (SUS) were also differentially regulated in CsSWEET7a transgenic lines. Immunohistochemical analysis demonstrated that CsAGA2 co-localized with CsSWEET7a in companion cells, indicating cooperation between AGA and CsSWEET7a in fruit phloem unloading. Our findings indicated that CsSWEET7a is involved in sugar phloem unloading in cucumber fruit by removing hexoses from companion cells to the apoplasmic space to stimulate the raffinose family of oligosaccharides (RFOs) metabolism so that additional sugars can be unloaded to promote fruit growth. This study also provides a possible avenue towards improving fruit production in cucumber.


A new strategy for the bioproduction of all ketohexoses was developed using hexitols as intermediates. Biocatalysts used to employ the strategy were D-tagatose 3-epimerase, which epimerizes ketohexoses at the C-3 position, and oxidoreductases, which catalyze oxidation-reduction reactions between ketohexoses and the corresponding hexitols. Arranging all the ketohexoses and hexitols in a symmetric ring and connecting them with 20 biochemical reactions, I was able to construct a design for the bioproduction of all the rare ketohexoses. Various aldose isomerases transform ketohexoses into the corresponding aldohexoses, so the strategy is useful for the bioproduction of all the rare hexose sugars. Furthermore, the design revealed that there are four routes to the L-hexose world from the D-hexose one. 041b061a72


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