Disaccharide

Sucrose, common table sugar, is a disaccharide made up of

fructose linked by a glycosidic bond to glucose.
From: Nutritional Pathophysiology of Obesity and its Comorbidities, 2017

Related terms:

Glycosaminoglycan, Carbohydrate, Hyaluronic Acid, Heparan Sulfate,

Polysaccharide, Oligosaccharide, Monosaccharide, Fructose, Galactose, Lactose

Carbohydrates: Chemistry and Classification

C. Stylianopoulos, in Encyclopedia of Human Nutrition (Third Edition), 2013

Disaccharides
Disaccharides consist of two monosaccharide units, linked together with

glycosidic bonds in the α or β orientation. The most important of them are

sucrose, lactose, and maltose. Sucrose is the most abundant and consists

of a molecule of α-glucose and β-fructose linked together (Figure 2(a)).

Lactose is found in milk and dairy products and consists of galactose and

glucose linked by a β-1,4-glycosidic bond (Figure 2(b)). Maltose is mainly

produced by partial hydrolysis of starch and consists of two glucose units

linked by an α-1,4-glycosidic bond (Figure 2(c)). Some nutritionally

important disaccharides and disaccharide derivatives and their

significance are outlined in Table 2.

Figure 2. The molecular structures of (a) sucrose, (b) lactose, and (c)
maltose.

Table 2. Some nutritionally important disaccharides and disaccharide

derivatives

Class Species Significance

Disaccharide Sucrose Constituent of fruits, vegetables,

and sweetener

Lactose Milk and dairy products

Maltose, Constituent of starch

isomaltose

Trehalose Food additive and constituent of

mushrooms

Lactulose Lactose derivative, laxative

Disaccharide Maltitol Constituent of starch, sweetener

alcohols
Lactitol Constituent of lactose, sweetener

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CARBOHYDRATES | Classification and Properties

R.F. Tester, J. Karkalas, in

Encyclopedia of Food Sciences and Nutrition (Second Edition), 2003

Disaccharides
Nomenclature
Disaccharides can be reducing (having a free carbonyl group) or

nonreducing. In the latter case, the two component monosaccharides are

linked at their respective anomeric centers, and therefore, the carbonyl

group is not available for reaction. Disaccharides are named as glycosides

where the aglycone is another monosaccharide. Reducing disaccharides

are named as substituted monosaccharides (Figure 10).

Figure 10. Formulae and nomenclature of three common disaccharides.

Sucrose does not have a free carbonyl group. The OH group on the
anomeric carbon atom of maltose and lactose can acquire either the α- or
the β-configuration. Both sugars mutarotate when dissolved in water, and
equilibrium is established after several hours. A few drops of ammonia
accelerate the rate of mutarotation, and a constant specific rotation is
rapidly attained.

Sucrose (saccharose) is by far the most important disaccharide (See

SUCROSE | Properties and Determination; SUCROSE | Dietary Importance;

SUGAR | Sugarcane; SUGAR | Sugarbeet; SUGAR | Palms and Maples;

SUGAR | Refining of Sugarbeet and Sugarcane). Lactose (See LACTOSE)

occurs in the milk of mammals but very rarely in the plant kingdom.

Trehalose (α-d-glucopyranosyl α-d-glucopyranoside) (nonreducing)

occurs in mushrooms and other fungi. Maltose is formed during the

mashing of malt (See MALT | Malt Types and Products; MALT | Chemistry

of Malting) in brewing and serves as a substrate for yeast in alcoholic

fermentation. It is also a component of high-maltose syrup. Cellobiose (β-

d-glucopyranosyl-(1→4)-d-glucose) (reducing) is formed by the

enzymatic hydrolysis of cellulose.

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Carbohydrates

Rylee T. Ahnen MS, ... Joanne Slavin PhD, RDN, in

Present Knowledge in Nutrition (Eleventh Edition), 2020

Disaccharides
Disaccharides are two monosaccharides that have been joined to one

another through a glycosidic bond, which is also sometimes called an

acetal bond, and occurs between hydroxyl groups on each of the

individual monosaccharides. Disaccharides are a major source of energy

in the diet and are typically thought of as the following three major

compounds: sucrose, lactose, and maltose.

Sucrose, commonly thought of as table sugar, is the most widely available

disaccharide and is the most commonly used naturally occurring

sweetener. Sucrose is composed of glucose and fructose, and while it

occurs naturally in some fruits and vegetables, it is most commonly

thought of in its refined form, which is primarily derived through the

processing of sugarcane or beets. Due to its unique structure, sucrose

cannot act as a reducing sugar. Reducing sugars are those sugars that have

a free aldehyde group or a free ketone group that allows them to act as a

reducing agent. The ability of a sugar to act as a reducing agent is

important in food processing and production because reducing sugars are

necessary for the Maillard reaction to take place. In the Maillard reaction,

reducing sugars and amino acids react and create desirable flavors, colors,

and textures in some food products. Lactose, which comprises of glucose

bonded to galactose, occurs naturally in milk and milk products. As

discussed later, lactose is a carbohydrate of concern for some individuals

for whom it is not well tolerated. Lastly, the compound maltose contains

two glucose molecules that are joined by an alpha bond. Maltose is

primarily formed through the partial hydrolysis of starches and other

polysaccharides. Because this process is needed in the production of

many alcoholic beverages (malted beverages), maltose is typically found

in beer and malt liquor.

Trehalose is another disaccharide, though it is a rather insignificant

carbohydrate in the diet. Trehalose is a nonreducing sugar that is found

primarily in fungi, yeasts, insects, and shellfish.

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Diet and Irritable Bowel Syndrome, with a Focus on
Appetite-Regulating Gut Hormones

Magdy El-Salhy, ... Trygve Hausken, in

Nutrition in the Prevention and Treatment of Abdominal Obesity, 2014

Poorly Absorbed Carbohydrates and Fibers

FODMAPs are short-chain carbohydrates that are poorly absorbed, and a

significant portion of these ingested carbohydrates enter the distal small

bowel and colon [103]. These sugars include fructose, lactose, sugar

alcohols (sorbitol, maltitol, mannitol, xylitol, and isomalt), fructans, and

galactans. Fructose and lactose are present in apples, pears, watermelon,

honey, fruit juices, dried fruits, and milk and milk products. Polyols are

used in low-calorie food products. Galactans and fructans are present in

wheat, rye, artichokes, asparagus, broccoli and Brussels sprouts, cabbage,

garlic, leeks, onions, legumes, lentils, and soy [90,91,104].

FODMAPs increase the osmotic pressure within the large intestine and

provide a substrate for bacteria fermentation, leading to gas production

and distension of the large intestine. An increase in the intraluminal

pressure can stimulate the release of serotonin and substance P into the

interstitial fluid. Serotonin activates the submucosal sensory branch of the

enteric nervous system (ENS), which conveys the sensation to the central

nervous system (CNS), probably causing abdominal pain and discomfort

[105–107]. Furthermore, serotonin controls gastrointestinal motility and

chloride secretion via interneurons and motor neurons, which may result

in motility and secretion disturbances [105–107]. Although increasing

dietary fiber intake is still recommended for patients with IBS, especially

those with IBS-C, clinical practice shows that this increases abdominal

pain, bloating, and distension [108]. However, it has been shown that

soluble fiber intake is effective in improving overall IBS symptoms and

has fewer side effects than insoluble fiber [44–46,109–111].

The fermentation of FODMAPs and insoluble fiber to produce gas and

intraluminal distention depends upon the composition of the intestinal

flora. A dominance of Clostridium spp. in the intestinal flora over

beneficial bacteria such as Lactobacillus and Bifidobacterium spp., which

do not produce gas upon fermenting carbohydrates, would worsen the IBS

symptoms [1]. On the other hand, consuming foods supplemented with

probiotics that contain these latter bacteria would increase tolerance to

both FODMAPs and fiber [1].

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Macronutrients

Laurence Cole, Peter R. Kramer, in

Human Physiology, Biochemistry and Basic Medicine, 2016

Disaccharides
Disaccharides are composed of two monosaccharide units linked together

by a glycosidic bond. The most common glycosidic bonds connecting

monosaccharide units are O-glycosidic bonds in which the oxygen from a

hydroxyl group becomes linked to the carbonyl carbon. Sugars may also

become linked to molecules by N-glycosidic bonds and other types of

glycosidic bonds. The configuration about the anomeric carbon can be

alpha or beta as discussed in Chapter 1.3. Some common disaccharides are

listed below (Table 5.1.4).

Table 5.1.4. Disaccharides

Disaccharide Common name Configuration Monosaccharides

Sucrose Table sugar β(1 → 2) Glucose-fructose

Lactose Milk sugar β(1 → 4) Galactose-glucose

Maltose Malt sugar α(1 → 4) Glucose-glucose

Isomaltose α(1 → 6) Glucose-glucose

Sucrose and maltose are digested in the small intestine by the enzyme

sucrase-isomaltase, which is composed of two subunits, one that

hydrolyzes sucrose and maltose and the other that hydrolyzes isomaltose.

Maltose is a product of the breakdown of starch by amylase. Lactose is

digested in human infants, children, and many adults by lactase. The

quantity of lactase secreted in many people may diminish with age.

Symptoms of intolerance include gas, belly pain, and bloating. Lactose-

free milk is leading to lactose intolerance because of the population’s

inability to digest lactose. Symptoms of lactose commercially available as

are lactase supplements that can be taken with milk or lactose-containing

dairy products.

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Lactose Maldigestion

B. Burke, ... O. Brown, in Reference Module in Biomedical Sciences, 2014

Lactose Digestion
Disaccharide digestion occurs on the brush border of the intestinal lining.

The lactase enzyme is bound to the plasma membrane and catalyzes the

cleavage of lactose into glucose and galactose. The physical proximity of

the lactose allows for the absorption of digested nutrients. Lactose must

be broken down into glucose and galactose prior to absorption of the

resultant monosaccharides (Figure 1) (Heyman, 2006).

Figure 1. Ingested lactose encounters the lactase enzyme on the brush

border of the small intestine. The enzyme breaks down lactose into its
monosaccharides, glucose, and galactose.

Reproduced with permission from Heyman, M., 2006. Lactose intolerance in infants,

children, and adolescents. J. Am. Acad. Pediatr. 118 (3), 1279–1286.

Lactase activity is restricted to the absorptive cells of the small intestine;

it is active at the highest level in the midjejunum. This digestion of lactose

via lactase is a hydrolysis reaction in which the glycosidic link in lactose is

broken by reacting with a water molecule. Once broken down into the

simple form of sugars in the duodenum and jejunum of the small

intestine, glucose and galactose are absorbed into the intestinal cells with

sodium using the same transporter (Hurley, 2010).

Absorption of the monosaccharides glucose and galactose involves

transport from the intestinal lumen, across the epithelium, and into the

vascular system. The transporter that carries glucose and galactose into

the blood is sodium-dependent and known as GLUT1. This transporter is

located on the side of plasma membrane that faces toward the lumen of

the epithelial cells. Both sodium and glucose must be present for the
transporter to be active; the transporter will not carry either molecule

alone. The basolateral membrane faces inside the cell, and away from the

lumen. On this plasma membrane is GLUT2, which allows diffusion of

both sugars out of the cell into the extracellular fluid and ultimately, into

the blood. The sugars are readily absorbed into the bloodstream and taken

to the liver. In the liver, the sugars are transported to other organs or

converted to lipid for storage. Through this mechanism, the liver helps to

regulate blood glucose levels (Hurley, 2010).

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Glycans and Glycosaminoglycans as Clinical

Biomarkers and Therapeutics - Part A

Lingling Xu, ... Lijuan Zhang, in

Progress in Molecular Biology and Translational Science, 2019

2.3 Chondroitin sulfate (CS)

The repeating disaccharide of CS has one glucuronic acid and one N-acetyl

galactosamine. Usually sulfation occurs in 4- and/or 6-positions in the

repeating disaccharide of CS. It has been demonstrated that in many

cancers both the sulfation degree and the sulfation position change in CS.

Sometime the quantity of CS in cancer patient plasmas is also different

from that of healthy control.

It has been reported that a progressive increase in the content of CS,

decrease in molecular weight, and increase in both nonsulfated and

disulfated CS disaccharides are associated with differentiation status of

hepatocellular carcinoma.71

The serum concentration of CS WF6 epitope is dramatically increased in

91 ovarian cancer patients at different stages of cancer development.72

Another report shows that elevated levels of peritumoral CS are predictive

of poor prognosis in patients treated by radical prostatectomy for early-

stage prostate cancer.73

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Carbohydrates, Alcohols, and Organic Acids

Martin Kohlmeier, in Nutrient Metabolism (Second Edition), 2015

Digestion and Absorption

The disaccharide sucrose (Glc α-[1>β2] Fru) is hydrolyzed by sucrose ot-

glucosidase (EC3.2.1.48), a component of the brush border enzyme

complex sucrase-isomaltase. The facilitative transporter GLUT5 (SLC2A5),

the sodium-dependent transporter SGLT4/SLC5A9 (Tazawa et al., 2005),

and to a lesser extent GLUT2 (SLC2A2), mediate Fru uptake from the

small-intestinal lumen, mainly the jejunum (Helliwell et al., 2000).

Diffusion and paracellular passage via glucose-activated solute drag also

may contribute to absorption. Large quantities (25 g) are poorly absorbed

and will cause malabsorption symptoms in as many as one-third of

healthy subjects (Born et al., 1994). GLUT2 (SLC2A2) facilitates the

transport of Fru out of enterocytes into interstitial fluid from where it

enters the portal bloodstream (Figure 6.9).

Figure 6.9. Intestinal absorption of fructose.

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Carbohydrate Digestion, Absorption, and Fiber

G. Livesey, in Reference Module in Biomedical Sciences, 2014

Lactulose
This disaccharide, 4-o-β-d-galactopyranosyl-β-d-fructofuranose, is

obtained by isomerization of lactose. It is neither absorbed nor digested in

the small intestine but is fermented in the colon. Both osmolality and

acidity from short-chain fatty acids in the colon aid peristalsis and the

passage of loosened, watery stools. Fermentation gasses also add bulk and

stool softening. Because of these effects, lactulose is therapeutic in

persons with constipation. By encouraging the growth of colonic

microbiota, which use ammonia, lactulose is also used in hospitals for the

treatment of hyperammonemia with some relief of accompanying hepatic

encephalopathy.

Lactulose is taken therapeutically as syrup. Polyols in drinks might be

expected to have similar effects, but drinks are not marketed. Polyols have

smaller effects when in foods than in drinks because the accompanying

solids slow stomach emptying and consequently slow the delivery of

polyol into the colon.

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Lactose

A.M. Shendurse, C.D. Khedkar, in Encyclopedia of Food and Health, 2016

Introduction
The disaccharide lactose occurs in milk, mainly free with a small extent as

a component of higher oligosaccharides. Its concentration in milk varies

with the mammalian source from 2.0% to 8.5%. Cow and goat milks

contain 4.5–4.8% and human milk about 7%. It is the primary

carbohydrate for developing mammals. In humans, lactose constitutes

40% of the energy consumed during nursing. The utilization of lactose for

energy must be preceded by hydrolysis to the constituent

monosaccharides, d-glucose and d-galactose. Milk also contains 0.3–0.6%

of lactose-containing oligosaccharides, many of which are important as

energy sources for growth of a specific variant of Lactobacillus bifidus,

which is the predominant component of the intestinal microbiota of

breast-fed infants.

Lactose is ingested through milk and other unfermented dairy products,

such as ice cream. Fermented dairy products, such as most yogurt, dahi,

and cheeses, contain less lactose because during fermentation, some of it

is converted into lactic acid. It stimulates intestinal adsorption and

retention of calcium. Lactose is not digested until it reaches the small

intestine, where the hydrolytic enzyme lactase is located. Lactase (β-

galactosidase) is a membrane-bound enzyme located in the brush border

epithelial cells of the small intestine. Lactase catalyzes the hydrolysis of

lactose into its constituent monosaccharides. Only monosaccharides

among the carbohydrates are absorbed from the intestines. Both d-

glucose and d-galactose are rapidly absorbed and enter the bloodstream.

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