Questions tagged [carbohydrates]

Carbohydrates are one of three classes of primary metabolites and thus natural products. They are polyhydroxylated hydrocarbons and their derivatives. Colloquially, they are known as sugars. This tag may be applied to all questions that concern carbohydrate species in solution, reaction mechanisms and structures.

The name carbohydrate suggests a structural formula of $\ce{C}_m\ce{(H2O)}_n$. They were historically considered to be hydrates of carbon; a view supported by their reaction with concentrated sulphuric acid which yields carbon. However, not all carbohydrates abide by this general formula.

Since carbohydrates usually contain a carbonyl group along with hydroxy groups, they show a rich isomer chemistry in aquaeous solution. Glucose, for example, can switch between $\unicode[Times]{x3B1}$-pyranose, $\unicode[Times]{x3B1}$-furanose, $\unicode[Times]{x3B2}$-pyranose, $\unicode[Times]{x3B2}$-furanose, open-chain and other minority forms. $64\,\%$ of glucose in solution is $\unicode[Times]{x3B2}$-pyranose, $35\,\%$ is in $\unicode[Times]{x3B1}$-pyranose.

Most carbohydrates are natural products and are considered primary metabolites; i.e. every organism is capable of producing them in one form or another. Colloquially, they are also known as sugars due to the sweet taste of some very abundant carbohydrate species such as glucose and saccharose. Since carbohydrates are the short-term cellular energy source, and since ribose and deoxyribose are part of the DNA, carbohydrates can be considered essential for all life forms.

Per definition, carbohydrates must contain at least three carbon atoms, which means that the two simplest carbohydrates are 1,3-dihydroxyacetone and glycerinaldehyde. There is no strict upper limit. Also, carbohydrates are not limited to the elements $\ce{C, H}$ and $\ce{O}$; e.g. glucosamine, in which an amino group has replaced a hydroxy group, is also a carbohydrate derivative and within the scope of this tag.

Simple building blocks, known as monosaccharides can be combined to form di- and polysaccharides such as lactose, saccharose, amylose or cellulose. Complex polysaccharides are often found in glycoproteins which in turn are often used as cellular receptors.

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How can 32 g of Gatorade powder contain 33 g of carbohydrates?

A screenshot of the nutrition facts of a can of Gatorade powder was posted on my Facebook feed: The label reads "Per 32 g (about 3 tbsp)", but if you read through the ingredients, the amount of carbohydrates listed exceed that of the serving size…
yuritsuki
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Identifying the D/L form of any aldose or ketose in cyclic form

I understand that the compound above is a ketose because it has a furanose ring. But, how do we know that it is a "D" form? Is there any general rule by which I can identify if any given aldose/ketose is in D/L form?
Gaurang Tandon
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Distinguish between glucose and Fructose samples

I am looking for a simple way to distinguish between glucose and fructose samples. Currently, I am doing that by melting temperature method. Can anybody suggest me some easy way to do that?
jacob wick
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Is there a way to faciliate remembering which are alpha/beta hemiacetals of sugars?

I understood the concept of hemiacetals quite well, but have considerable trouble remembering which are called $\alpha$ or $\beta$ respectively. Is there some concept/mnemonic/common reaction/something else to faciliate remembering this convention?
caconyrn
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Are substituted sugar/carbohydrate derivatives such as sucralose still sugars/carbohydrates?

Sucralose is made from sucralose, with chlorination of 3 of the hydroxyl groups. If broken up into the 2 saccharide-type units, you'll get 1,6-dichloro-1,6-dideoxyfructose and 4-chloro-4-deoxy-D- galactose. Firstly, are those 2 compounds considered…
smw
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Why are polysaccharides non-reducing sugars?

My book says that polysaccharides are non-reducing sugars, and they form of condensation of >6 molecules of monosaccharides. The condensation involves the carbonyl groups of the sugars, leaving only one free carbonyl group at the end of a big…
Asmaa
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Hydrophobicity of Polysaccharides

Are polysaccharides generally considered to be hydrophobic and/or hydrophilic? My reasoning is that although they have polar groups/electronegative atoms, the polymeric nature of polysaccharides excludes water so I'm leaning towards them being…
user29171
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Do all reducing sugars show mutarotation?

Do all reducing sugars show mutarotation? I studied that for a sugar to be reducing it must possess a free aldehydo or keto group. Also, for a mutarotation interconversion between α- and β-forms of compound are required. If there is a free aldehydo…
IITM
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What are the differences between D and L glucopyranose?

I have just studied the concept of cyclotron in carbohydrates. My reference book used Glucose as an example and began by saying we can find D-glucose or L-glucose: Depending on what enantiomer we have, we will get opposite chair conformations at…
Bee
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Reducing sugar among the given compounds

The question is to determine which of the following sugars is not reducing? I have the idea that in case of disaccharide sugars in which the monosachharide units are bonded via the carbon containing aldehydic group are non reducing.However the…
Pink
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Quantify Sweetness?

My textbook gives many examples of sweetening agents. For Alitame it says its 2000 times sweeter than cane sugar. Aspartame is 100 times sweeter than sugar. I am wondering how they quantify sweetness?
Black Jack 21
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What types of glycosidic bonds are in oligosaccharides that occurs naturally not in the lab?

An oligosaccharide is a carbohydrate formed by two or more monosaccharides. If both monosaccharides are pyranose types, they can bond through ($\alpha$ or $\beta$)1-4 or ($\alpha$ or $\beta$)1-6. If one monosaccharide of them is of furanose type,…
Another.Chemist
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Stability of alpha vs beta anomer in glucose

As per my knowledge, there seems to be 2 main factors influencing the stability of alpha vs beta anomers of glucose: H - bonding Considering this, beta anomer would be more stable due to the possible h bond between c1 - oh and c6 - oh Anomeric…
aakraj064
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Haworth's research of glucose

Firstly haworth used CH3I/Ag2O with glucose which replaced 5 H by CH3 forming a acetal which locked the anomer and stopped the equilibirium of ring chain tautomerism. Under dilute acidic conditions acetal group hydrolyze and ethers do not. So my…
aryan bansal
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Will mixing methyl 2-cyanoacrylate and cellulose make the cellulose harden quickly?

The other day I was gluing together cotton fabric with methyl 2-cyanoacrylate (superglue) and the fabric started heating up and then eventually began smoking. I have been working on making a 2-part plastic-like substance for personal reasons for…
WCIS
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