Ketoses

If a monosaccharide has a carbonyl function on one of the inner atoms of the carbon chain it is classified as a ketose. Dihydroxyacetone may not be a sugar, but it is included as the ketose analog of glyceraldehyde. The carbonyl group is commonly found at C-2, as illustrated by the following examples (chiral centers are colored red). As expected, the carbonyl function of a ketose may be reduced by sodium borohydride, usually to a mixture of epimeric products. D-Fructose, the sweetest of the common natural sugars, is for example reduced to a mixture of D-glucitol (sorbitol) and D-mannitol, named after the aldohexoses from which they may also be obtained by analogous reduction. Mannitol is itself a common natural carbohydrate.
Although the ketoses are distinct isomers of the aldose monosaccharides, the chemistry of both classes is linked due to their facile interconversion in the presence of acid or base catalysts. This interconversion, and the corresponding epimerization at sites alpha to the carbonyl functions, occurs by way of an enediol tautomeric intermediate. By clicking on the diagram, an equation illustrating these isomerizations will be displayed.

Because of base-catalyzed isomerizations of this kind, the Tollens' reagent is not useful for distinguishing aldoses from ketoses or for specific oxidation of aldoses to the corresponding aldonic acids. Oxidation by HOBr is preferred for the latter conversion.

مواضيع ذات صلة

تصنيف الكاربوهيدرات classification of carbohydrate

تعريف الكاربوهيدرات Definition of carbohydrates

دورة الكلايوكسليت Glyoxylate cycle

أيض الكاربوهيدرات

أصناف الكاربوهيدرات Classification of carbohydrates

الكاربوهيدرات

فرط كيتون الجسم هو تلاؤم ايضي تجاه الجوع

يتوفر للأنسجة مصدر مستمر من الوقود خلال الجوع

الجلوكوز هو ضرورة ايضية للمخ والكريات الحمراء في جميع الحالات التغذوية

ان الاستعمال الامثل للأجسام الكيتونية والاحماض الدهنية الحرة يوفر الجلوكوز من اجل وظائفه الاساسية

الجلوكوز هو طليعة جميع السكاكر الآمينية (الهكسوزأمينات)

يترافق وجود الفركتوز والسوربيتول في عدسة العض مع الساد (Cataract) السكري