D-ribose: health benefits of the supplement. Monosaccharides: ribose, deoxyribose, glucose, fructose. The concept of spatial isomers of carbohydrates. Cyclic forms of Ribose monosaccharides industrial use

Ribose is a natural carbohydrate that has many important physiological functions and influences fiber metabolism and synthesis. But its presence in our body is limited. Does this mean that supplementation with ribose should lead to improved athletic performance?

Why is ribose so important?

Ribose is an integral part of riboflavin (vitamin B2), which in turn is part of two enzymes involved in aerobic energy metabolism. It is also used in the synthesis of certain nucleotides such as adenosine triphosphate (ATP), the main source of energy for muscle contraction. Our ability to handle high-intensity loads depends on the amount of ATP in the muscles and its resynthesis during exercise. Finally, ribose helps to collect nucleic acids - deoxyribonucleic acid (DNA) and ribonucleic acid (RNA).

DNA stores the genetic information needed to specify the structure of proteins, while RNA is programmed with the timing and sequence of cell and fiber synthesis. It also determines the structure of chromosomes and genes. RNA helps to decipher genetic information for protein synthesis. Our body can get ribose from normal food or synthesize it from glucose. However, in ordinary food there are only traces of ribose, and its synthesis is only a secondary metabolic process in glucose metabolism. Therefore, there is quite a bit of ribose in the body.

Consuming ribose is recommended to increase ATP levels. As an experiment, it was used to treat patients with glucose synthesis deficiency and coronary heart disease. For example, Wagner et al. (1) report that oral glucose intake (3 grams every 10 minutes), starting one hour before exercise and prior to final testing (that is, only 21-24 grams), increases the availability of ATP in patients with a deficiency of the myodenilate enzyme. diaminase (its deficiency complicates the resynthesis of ATP during exercise).

Riml and colleagues (2) report that taking ribose - 60 grams daily for three days - postponed the onset of ischemia during sports in people suffering from various coronary artery diseases. In addition, Gross and his co-workers (3) reported that ribose (two grams orally every five minutes during a 30-minute submaximal workout) can inhibit the normal release of hypoxanthine (a measure of ATP breakdown). This suggests that ribose may have ergogenic properties and affect energy metabolism.

The use of ribose in sports

After such observations, ribose began to be recommended for use by athletes. It was hailed as the newest drug to displace creatine from the scene. Ribose is sold in both powder and liquid form, mixed with other nutrients (carbohydrates, creatine, glutamine) and separately. The recommended dosage is usually 1.5-3 grams of ribose before and / or after exercise. Some manufacturers recommend taking ribose during a creatine load (that is, 1.5-3 grams of ribose with five grams of creatine four times a day for five days), and then switching to a maintenance dose once a day.

D-ribose is a simple sugar that is synthesized in the body from glucose and is found in the DNA and RNA of all living organisms.

DNA is a chain of nucleotides that stores genetic information about every cell in the body, while RNA translates this genetic information into the proteins that make up the body.

D-ribose formula

D-ribose is also responsible for the production of ATP ( adenosine triphosphate). ATP is the main source of energy in the body.

The list of ATP functions is almost endless. ATP is the main source of energy used in resistance training.

D-ribose is also a component of vitamin B2 (riboflavin). Vitamin B2 is an important component of the molecules involved in energy metabolism.

Benefits of D-ribose

The main idea that promoted by manufacturers D-ribose, is that an increase in the consumption of this sugar necessarily leads to the fact that the body synthesizes more of the substances described above, which are important sources of energy.

Increasing the amount of ATP available increases energy storage and strength during exercise and improves recovery from exercise.

Under normal conditions, the body is forced to re-synthesize these compounds when needed, and this is where D-ribose can help it.

In theory, you should be able to train longer, lift heavier weights, and recover faster between workouts.

What does real research say?

So far, research results on D-ribose and its effects on strength, energy, and lean muscle mass are conflicting, to say the least.

To begin with, most of the studies that talk about the positive effects of consuming D-ribose have been conducted on individuals who initially had a disrupted synthesis of this substance.

Obviously, the use of D-ribose by such people will have some positive effects, but this does not tell us anything about the effects on ordinary healthy athletes.

One study in untrained people found that consuming two grams of D-ribose every five minutes during intense exercise led to an increase in lactic acid production.

In another study, male subjects received 5 grams of D-ribose before and after bench press. They did show a noticeable increase in strength compared to the placebo group, however, most other studies involving athletes showed mediocre or no results.

Most of the real reviews about D-ribose are negative, with users receiving mixed results, which are mostly negative.

There are two more reasons that theoretically explain why taking D-ribose would be ineffective.

1) During the natural synthesis of D-ribose in the body through the so-called "pentose phosphate pathway", a substance called NADP (Nicotinamide Adenine Dinucleotide Phosphate) is also synthesized. These two substances are always synthesized together from the same chain and in a certain ratio: 2 NADPH molecules per 1 ribose molecule.

It is possible that the body actually needs more NADP than D-ribose, and D-ribose is a by-product of the synthesis of NADP from this chain. For this reason, the use of D-ribose alone, even in large quantities, cannot produce the same effect as its natural synthesis in the body.

2) In the process of natural synthesis of D-ribose, an additional phosphate group is always attached to it. This additional group dramatically changes the function of the molecule, and this is the reason for the subsequent changes in the body. Therefore, consuming d-ribose alone cannot produce the same effects.

Summing up the benefits of D-ribose

At this point, it cannot be argued that ribose supplementation can improve body shape or performance in the gym.

Research results are insufficient, and real reviews are usually negative.

Perhaps future research will reveal some of the real benefits of D-ribose that are currently not known.

Monosaccharides: classification; stereoisomerism, D– and L – series; open and cyclic forms on the example of D-glucose and 2-deoxy-D-ribose, cyclo-oxotautomerism; mutarotation. Representatives: D-xylose, D-ribose, D-glucose, 2-deoxy-D-ribose, D-glucosamine.

Carbohydrates- heterofunctional compounds, which are aldehyde or ketone monohydric alcohols or their derivatives. The class of carbohydrates includes a variety of compounds - from low molecular weight, containing from 3 to 10 carbon atoms, to polymers with molecular weights of several million. In relation to acid hydrolysis and physicochemical properties, they are divided into three large groups: monosaccharides, oligosaccharides and polysaccharides .

Monosaccharides(monoses) - carbohydrates that are unable to undergo acid hydrolysis to form simpler sugars. Monoses classify by the number of carbon atoms, the nature of the functional groups, stereoisomeric series and anomeric forms. By functional groups monosaccharides are subdivided into aldoses (contain an aldehyde group) and ketosis (contain a carbonyl group).

By number of carbon atoms in the chain: trioses (3), tetroses (4), pentoses (5), hexoses (6), heptoses (7), etc. up to 10. The most important are pentoses and hexoses. By configuration of the last chiral atom carbon monosaccharides are divided into D- and L-series stereoisomers. As a rule, D-series stereoisomers (D-glucose, D-fructose, D-ribose, D-deoxyribose, etc.) are involved in metabolic reactions in the body.

In general, the name of an individual monosaccharide includes:

A prefix describing the configuration of all asymmetric carbon atoms;

A digital syllable that defines the number of carbon atoms in the chain;

Suffix - oza - for aldoses and - uloza - for ketosis, and the locant of the oxo group is indicated only if it is not at the C-2 atom.

Structure and stereoisomerism monosaccharides.

Monosaccharide molecules contain several centers of chirality; therefore, there are a large number of stereoisomers corresponding to the same structural formula. Thus, the number of stereoisomers of aldopentoses is eight ( 2 n , where n = 3 ), including 4 pairs of enantiomers. Aldohexoses will already have 16 stereoisomers, i.e. 8 pairs of enantiomers, since their carbon chain contains 4 asymmetric carbon atoms. These are allose, altrose, galactose, glucose, gulose, idose, mannose, talose. Ketohexoses contain one chiral carbon atom less than the corresponding aldoses, so the number of stereoisomers (2 3) decreases to 8 (4 pairs of enantiomers).

Relative configuration monosaccharides determined by configuration the chiral carbon atom farthest from the carbonyl group by comparison with the configuration standard - glyceraldehyde. When the configuration of this carbon atom coincides with the configuration of D-glyceraldehyde, the monosaccharide is generally referred to as the D-series. Conversely, when coinciding with the configuration of the L-glyceraldehyde, the monosaccharide is considered to belong to the L-series. Each aldose of the D-series corresponds to an enantiomer of the L-series with the opposite configuration of all chirality centers.

(! ) The position of the hydroxyl group at the last center of chirality on the right indicates that the monosaccharide belongs to the D-series, on the left - to the L-series, i.e., the same as in the stereochemical standard - glycerolic aldehyde.

Natural glucose is a stereoisomer D-series... In equilibrium, glucose solutions have a right-handed rotation (+ 52.5º), therefore glucose is sometimes called dextrose. The name grape sugar is due to the fact that it is most contained in grape juice.

Epimers called diastereomers of monosaccharides, differing in the configuration of only one asymmetric carbon atom. The epimer of D-glucose at C 4 is D-galactose, and at C 2 is mannose. Epimers in an alkaline medium can pass into each other through the enediol form, and this process is called epimerization .

Tautomerism of monosaccharides. Studying properties glucose showed:

1) absorption spectra of glucose solutions, there is no band corresponding to the aldehyde group;

2) glucose solutions do not give all reactions to the aldehyde group (they do not interact with NaHSO 3 and fuchsin sulphurous acid);

3) when interacting with alcohols in the presence of "dry" HCl, glucose adds, unlike aldehydes, only one equivalent of alcohol;

4) freshly prepared glucose solutions mutarot within 1.5–2 hours the angle of rotation of the plane of the polarized light is changed.

Cyclic the forms of monosaccharides are cyclic by chemical nature semi-acetals , which are formed when the aldehyde (or ketone) group interacts with the alcohol group of the monosaccharide. As a result of intramolecular interaction ( A N mechanism ) the electrophilic carbon atom of the carbonyl group is attacked by the nucleophilic oxygen atom of the hydroxyl group. Thermodynamically more stable five-membered ( furanose ) and six-membered ( pyranose ) cycles. The formation of these cycles is associated with the ability of the carbon chains of monosaccharides to adopt a pincer-like conformation.

The graphical representations of cyclic forms presented below are called Fisher's formulas (you can also find the name "Collie-Tollens formula").

In these reactions, the C 1 atom from prochiral, as a result of cyclization, becomes chiral ( anomeric center).

Stereoisomers differing in the configuration of the C-1 atom aldose or C-2 ketosis in their cyclic form are called anomers , and the carbon atoms themselves are called anomeric center .

The OH group, which appears as a result of cyclization, is hemiacetal. It is also called a glycosidic hydroxyl group. In terms of properties, it differs significantly from the rest of the alcohol groups of the monosaccharide.

The formation of an additional chiral center leads to the emergence of new stereoisomeric (anomeric) α- and β-forms. α-Andimensional form is called one in which the hemiacetal hydroxyl is located on the same side as the hydroxyl at the last chiral center, and β-form - when the hemiacetal hydroxyl is on the other side than the hydroxyl at the last chiral center. 5 mutually transitioning tautomeric forms of glucose are formed. This type of tautomerism is called cyclo-oxo-tautomerism ... Tautomeric forms of glucose are in a state of equilibrium in solution.

In solutions of monosaccharides prevails cyclic hemiacetal form (99.99%) as more thermodynamically advantageous. The acyclic form containing the aldehyde group accounts for less than 0.01%; therefore, there is no reaction with NaHSO 3, the reaction with fuchsine sulfuric acid, and the absorption spectra of glucose solutions do not show the presence of a band characteristic of the aldehyde group.

Thus, monosaccharides - cyclic hemiacetals of aldehyde or ketone polyhydric alcohols existing in solution in equilibrium with their tautomeric acyclic forms.

In freshly prepared solutions of monosaccharides, the phenomenon is observed mutarotations - changes in time of the angle of rotation of the plane of polarization of light . Anomeric α- and β-forms have different angles of rotation of the plane of polarized light. Thus, crystalline α, D-glucopyranose, when dissolved in water, has an initial rotation angle of + 112.5º, and then it gradually decreases to + 52.5º. If β, D-glucopyranose is dissolved, its initial rotation angle is + 19.3º, and then it increases to + 52.5º. This is due to the fact that, for some time, an equilibrium is established between the α- and β-forms: 2/3 of the β-form → 1/3 of the α-form.

The preference for the formation of one or another anomer is largely determined by their conformational structure. The most favorable conformation for the pyranose cycle is armchairs , and for the furanose cycle - envelope or twist -conformation. The most important hexoses - D-glucose, D-galactose and D-mannose - exist exclusively in the 4C 1 conformation. Moreover, D-glucose of all hexoses contains the maximum number of equatorial substituents in the pyranose ring (and all of its β-anomers).

In the β-conformer, all substituents are in the most favorable equatorial position; therefore, this form is 64% in solution, and the α-conformer has an axial arrangement of the hemiacetal hydroxyl. It is the α-conformer of glucose that is contained in the human body and participates in metabolic processes. A polysaccharide, fiber, is built from the β-conformer of glucose.

Haworth's formulas... Fischer's cyclic formulas successfully describe the configuration of monosaccharides, but they are far from the real geometry of molecules. In the perspective formulas of Heworth, the pyranose and furanose cycles are depicted in the form of flat regular polygons (respectively, a hex or pentagon) lying horizontally. The oxygen atom in the cycle is located at a distance from the observer, and for pyranose it is in the right corner.

Hydrogen atoms and substituents (mainly CH 2 OH groups, if any, and he) are located above and below the plane of the cycle. The symbols for carbon atoms, as is customary when writing formulas for cyclic compounds, do not show. As a rule, hydrogen atoms with bonds to them are also omitted. For clarity, the C-C links, which are closer to the observer, are sometimes shown with bold lines, although this is not necessary.

To pass to the Hewors' formulas from Fisher's cyclic formulas, the latter must be transformed so that the oxygen atom of the cycle is located on the same straight line with the carbon atoms included in the cycle. If the transformed Fisher's formula is placed horizontally, as required by the writing of the Howorth formulas, then the substituents to the right of the vertical line of the carbon chain will be below the plane of the cycle, and those to the left will be above this plane.

The transformations described above also show that the hemiacetal hydroxyl is located under the plane of the cycle in the α-anomers of the D series, and above the plane in β-anomers. In addition, the side chain (at C-5 in pyranoses and at C-4 in furanoses) is located above the plane of the cycle, if it is bonded to a carbon atom of the D-configuration, and below, if this atom has an L-configuration.

Representatives.

D -Xylose - "wood sugar", a monosaccharide from the group of pentoses with the empirical formula C 5 H 10 O 5, belongs to aldoses. It is contained in plant embryos as an ergastic substance, and is also one of the monomers of the hemicellulose cell wall polysaccharide.

D-Ribose is a type of simple sugars that form the carbohydrate backbone of RNA, thus controlling all life processes. Ribose is also involved in the production of adenosine triphosphoric acid (ATP) and is one of its structural components.

2 – Deoxy – D – ribose - a component of deoxyribonucleic acids (DNA). This historically formed name is not strictly nomenclature, since the molecule contains only two centers of chirality (excluding the C-1 atom in the cyclic form), therefore this compound can be called 2-deoxy-D-arabinose with equal right. A more correct name for the open form: 2-deoxy-D-erythro-pentose (D-erythro-configuration is highlighted in color).

D-glucosamine – a substance produced by the cartilage tissue of the joints is a component of chondroitin and is part of the synovial fluid.

Monosaccharides: open and cyclic forms by the example of D-galactose and D-fructose, furanose and pyranose; - and β-anomers; the most stable conformations of the most important D-hexopyranose. Representatives: D-galactose, D-mannose, D-fructose, D-galactosamine (question 1).

Tautomeric forms of fructose are formed in the same way as tautomeric forms of glucose, by the reaction of intramolecular interaction (A N). The electrophilic center is the carbon atom of the carbonyl group at C 2, and the nucleophile is the oxygen of the OH group at the 5th or 6th carbon atom.

Representatives.

D-galactose – in animals and plants, including some microorganisms. It is part of the disaccharides - lactose and lactulose. When oxidized, forms galactonic, galacturonic and mucous acids.

D-mannose – a component of many polysaccharides and mixed biopolymers of plant, animal and bacterial origin.

D-fructose - monosaccharide, ketohexose, only the D-isomer is present in living organisms, in free form - in almost all sweet berries and fruits - it is included in sucrose and lactulose as a monosaccharide unit.

"

Professional athletes and those looking to significantly improve their athletic performance have long appreciated the benefits of sports nutrition and nutritional supplements that can increase muscle endurance and strength, as well as increase muscle volume and speed up recovery. Today on the sports nutrition market there is a fairly wide variety of sports nutritional supplements, each of which has its own individual properties and characteristics. In order to obtain the desired result, it is necessary to carefully approach the choice of sports nutrition, giving preference to the one that best suits your requirements and will have the desired effect. One of the novelties in the world of sports nutritional supplements is ribose, which is gradually gaining recognition and popularity among athletes.

What is ribose

Ribose is a natural carbohydrate that is quite common in life, however, the content of ribose in our body is limited, despite the fact that it is a useful substance that takes part in the course of metabolic processes and has a very large number of properties and physiological functions that affect fiber synthesis and metabolism. As you know, ribose is a part of nucleic acids and acts as an energy source. That is why it is used as a sports supplement for intense physical activity that requires a lot of energy. In addition, ribose contributes to the early recovery of damaged muscle tissues, thanks to which they are able to cope with heavy loads. Regular use of ribose can increase endurance and performance, as well as get rid of unwanted effects in the form of prolonged muscle soreness after intense sports activities.

Properties of ribose

As mentioned earlier, ribose has a large number of properties and has a positive effect on the processes occurring in the human body. She takes part in aerobic energy metabolism, being an integral part of vitamin B2. Ribose is involved in the synthesis of certain nucleotides, which are the source of energy required for muscle contraction. In addition, it promotes the accumulation of nucleic acids in the body, which are responsible for the sequence of synthesis of fibers and individual cells. It is also worth mentioning that it is ribose that determines the structure of genes and chromosomes, thereby accelerating the process of decoding the genetic information necessary for protein synthesis. Often, ribose is used as a prophylactic agent for coronary heart disease, increasing the level of glucose in the body. This food supplement can act as an antioxidant that fights free radicals.

When it comes to sports, ribose accelerates the body's absorption of creatine and improves performance and endurance. When ribose is used as a sports supplement, the body's recovery process after intense exertion is improved, reducing this period to several days. In preparation for a competition, it is necessary to replenish the reserves of ribose in the body, especially for those who frequent the gym or are engaged in powerlifting.

The use of ribose

More recently, ribose has been released as a standalone sports nutritional supplement that can be in powder or liquid form. Despite all the benefits of this substance, ribose is recommended to be taken in combination with other sports supplements, since it can significantly enhance their effect.

The most successful combination with ribose is creatine. This mixture increases the absorption of creatine, which is necessary to restore muscle tissue and increase the body's endurance, and also significantly increases strength performance, so that you can cope with heavy loads without harm to health. Ribose can be found not only as a separate supplement, but also as part of ready-made complexes. It is most commonly mixed with creatine, carbohydrates, and glutamine. When choosing sports nutrition for yourself, pay attention to the percentage of the elements that make up it, giving preference to those in which they are as balanced as possible.

Dosage and mode of taking ribose

Despite all its usefulness, ribose is necessary as an additional nutritional supplement only for those who regularly expose their body to intense physical activity. The minimum amount of ribose recommended for athletes is 2.2 grams per day, but some manufacturers advise increasing this number to four grams in order to improve results. Typically, ribose is taken once a day, shortly before or after training. However, when using ribose in combination with creatine, you need to consume 1.5 grams of ribose four times a day for five days, combining it with the reception of creatine. After completing the course, you should return to the usual regimen of taking ribose. In some cases, to enhance the effect, ribose is combined not only with creatine, but also with whey protein, which is necessary for muscle recovery and fiber regeneration.

Possible side effects of ribose

In the process of taking ribose, like any other sports nutritional supplements, it is necessary to adhere to certain recommendations, observing the regimen and dosage. In case of an overdose or individual intolerance, ribose can cause an allergic reaction, the severity of which depends on the dose of ribose consumed and its concentration in sports nutrition. In some cases, ribose can cause breathing problems and gastrointestinal distress. That is why, one should not neglect the recommendations and use ribose in large quantities, hoping for more rapid results.

Makhnonosova Ekaterina
for women's magazine website

When using and reprinting the material, an active link to the women's online magazine is required

Carbohydrate intake is a source of controversy among many sports nutritionists today. Some believe that the amount of carbohydrates should be strictly limited, while others draw our attention to the need to monitor the glycemic indices (indicators of the effect of a food product on the blood sugar level after eating it) of food …….

Carbohydrate intake is a source of controversy among many sports nutritionists today. Some believe that the amount of carbohydrates should be strictly limited, while others draw our attention to the need to monitor the glycemic indices (indicators of the effect of a food on the blood sugar level after eating it) of food.

One of the latest advances in carbohydrate foods with special properties is ribose. But does ribose really help you achieve high results in strength sports so effectively?

Ribose (D-ribose) is a monosaccharide (simple sugar) that is quite common in nature. It is known that it is an integral part of a nucleic acid, namely RNA. DNA molecules contain its derivative - deoxyribose. The four main nucleotides - Guanosine, Adenosine, Thymine and Cytosine - contain ribose residues in the molecules.

Adenosine is the most important nucleotide for muscle activity, and is part of adenosine triphosphate (ATP), a nucleotide that plays an important role in the metabolism of energy and substances in living organisms. ATP is the main source of energy during intense muscle activity. If the duration of the movements is seconds (conditions typical for strength work), and the load is close to the limit, the muscles are provided with energy precisely due to ATP. Some medical research suggests that ribose supplementation (10 to 60 grams per day) may increase the availability of ATP in people with certain conditions and protect against ischemia (when oxygen is reduced to tissues) and others.

In animal studies, the intake of ribose accelerated the synthesis of nucleotides in both working and non-working muscles of rats 3-4 times. In another study, ribose was found to be able to restore nucleotides to near normal levels over a period of 12 to 24 hours of intense work.

Malonos Yaroslav, 1990,
candidate master of sports in bodybuilding

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