Amylose

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Amylose
Amylose2.svg
Names
IUPAC name
(1→4)-α-D-Glucopyranan
Identifiers
ChEBI
ChemSpider
  • None
ECHA InfoCard 100.029.702 OOjs UI icon edit-ltr-progressive.svg
UNII
Properties
Variable
Molar mass Variable
AppearanceWhite powder
Insoluble [1]
Hazards
NFPA 704 (fire diamond)
NFPA 704.svgHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Amylose is a polysaccharide made of α-D-glucose units, bonded to each other through α(1→4) glycosidic bonds. It is one of the two components of starch, making up approximately 20–25% of it. Because of its tightly packed helical structure, amylose is more resistant to digestion than other starch molecules and is therefore an important form of resistant starch. [2]

Contents

Structure

Amylose A is a parallel double-helix of linear chains of glucose AmyloseA.gif
Amylose A is a parallel double-helix of linear chains of glucose

Amylose is made up of α(1→4) bound glucose molecules. The carbon atoms on glucose are numbered, starting at the aldehyde (C=O) carbon, so, in amylose, the 1-carbon on one glucose molecule is linked to the 4-carbon on the next glucose molecule (α(1→4) bonds). [3] The structural formula of amylose is pictured at right. The number of repeated glucose subunits (n) is usually in the range of 300 to 3000, but can be many thousands.

There are three main forms of amylose chains can take. It can exist in a disordered amorphous conformation or two different helical forms. It can bind with itself in a double helix (A or B form), or it can bind with another hydrophobic guest molecule such as iodine, a fatty acid, or an aromatic compound. This is known as the V form and is how amylopectin binds to amylose in the structure of starch. Within this group, there are many different variations. Each is notated with V and then a subscript indicating the number of glucose units per turn. The most common is the V6 form, which has six glucose units a turn. [4] V8 and possibly V7 forms exist as well. These provide an even larger space for the guest molecule to bind. [5]

This linear structure can have some rotation around the phi and psi angles, but for the most part bound glucose ring oxygens lie on one side of the structure. The α(1→4) structure promotes the formation of a helix structure, making it possible for hydrogen bonds to form between the oxygen atoms bound at the 2-carbon of one glucose molecule and the 3-carbon of the next glucose molecule. [6]

Fiber X-ray diffraction analysis coupled with computer-based structure refinement has found A-, B-, and C- polymorphs of amylose. Each form corresponds to either the A-, the B-, or the C- starch forms. A- and B- structures have different helical crystal structures and water contents, whereas the C- structure is a mixture of A- and B- unit cells, resulting in an intermediate packing density between the two forms. [7]

Physical properties

Because the long linear chains of amylose more readily crystallize than amylopectin (which has short, highly branched chains), high-amylose starch is more resistant to digestion. [8] Unlike amylopectin, amylose is insoluble in water. [9] [10] It also reduces the crystallinity of amylopectin and how easily water can infiltrate the starch. [6] The higher the amylose content, the less expansion potential and the lower the gel strength for the same starch concentration. This can be countered partially by increasing the granule size. [11] [12]

Function

Amylose is important in plant energy storage. It is less readily digested than amylopectin; however, because of its helical structure, it takes up less space than amylopectin. As a result, it is the preferred starch for storage in plants. It makes up about 30% of the stored starch in plants, though the percentage varies by species and variety. [13]

The digestive enzyme α-amylase breaks down starch molecules into maltotriose and maltose, which can be used as sources of energy.

Amylose is also an important thickener, water binder, emulsion stabilizer, and gelling agent in industrial and food-based contexts. Loose helical amylose chains have a hydrophobic interior that can bind to hydrophobic molecules such as lipids and aromatic compounds. The one problem with this is that, when it crystallizes or associates, it can lose some stability, often releasing water in the process (syneresis). When amylose concentration is increased, gel stickiness decreases but firmness increases. When other things, including amylopectin, bind to amylose, the viscosity can be affected, but incorporating κ-carrageenan, alginate, xanthan gum, or low-molecular-weight sugars can reduce the loss in stability. The ability to bind water can add substance to food, possibly serving as a fat replacement. [14] For example, amylose is responsible for causing white sauce to thicken, but, upon cooling, the solid and the water will partly separate. Amylose is known for its good film-forming properties, useful in food packaging. Excellent film-forming behavior of amylose was studied already in 1950s. [15] Amylose films are better for both barrier properties [16] and mechanical properties when compared to the amylopectin films. [17]

In a laboratory setting, it can act as a marker. Iodine molecules fit neatly inside the helical structure of amylose, binding with the starch polymer that absorbs certain known wavelengths of light. Hence, a common test is the iodine test for starch. If starch is mixed with a small amount of yellow iodine solution, a blue-black color will be observed. The intensity of the color can be tested with a colorimeter, using a red filter to discern the concentration of starch present in the solution. It is also possible to use starch as an indicator in titrations involving iodine reduction. [18] It is also used in amylose magnetic beads and resin to separate maltose-binding protein. [19]

Recent studies

High-amylose varieties of rice, the less sticky long-grain rice, have a much lower glycemic load, which could be beneficial for diabetics. [20]

Researchers have identified the Granule Bound Starch Synthase (GBSS) as the enzyme that specifically elongates amylose during starch biosynthesis in plants. [21] The waxy locus in maize encodes for the GBSS protein. [21] Mutants lacking the GBSS protein produce starch containing only amylopectin, such as in waxy corn. In Arabidopsis leaves, another gene, encoding the Protein Targeting to STarch (PTST) protein, is required in addition to GBSS for amylose synthesis. Mutants lacking either protein produce starch without amylose. [22] Genetically modified potato cultivar Amflora by BASF Plant Science was developed to not produce amylose.

See also

Related Research Articles

<span class="mw-page-title-main">Glucose</span> Naturally produced monosaccharide

Glucose is a sugar with the molecular formula C6H12O6. It is overall the most abundant monosaccharide, a subcategory of carbohydrates. It is mainly made by plants and most algae during photosynthesis from water and carbon dioxide, using energy from sunlight. It is used by plants to make cellulose, the most abundant carbohydrate in the world, for use in cell walls, and by all living organisms to make adenosine triphosphate (ATP), which is used by the cell as energy.

<span class="mw-page-title-main">Polysaccharide</span> Long carbohydrate polymers such as starch, glycogen, cellulose, and chitin

Polysaccharides, or polycarbohydrates, are the most abundant carbohydrates found in food. They are long-chain polymeric carbohydrates composed of monosaccharide units bound together by glycosidic linkages. This carbohydrate can react with water (hydrolysis) using amylase enzymes as catalyst, which produces constituent sugars. They range in structure from linear to highly branched. Examples include storage polysaccharides such as starch, glycogen and galactogen and structural polysaccharides such as hemicellulose and chitin.

<span class="mw-page-title-main">Starch</span> Glucose polymer used as energy store in plants

Starch or amylum is a polymeric carbohydrate consisting of numerous glucose units joined by glycosidic bonds. This polysaccharide is produced by most green plants for energy storage. Worldwide, it is the most common carbohydrate in human diets, and is contained in large amounts in staple foods such as wheat, potatoes, maize (corn), rice, and cassava (manioc).

<span class="mw-page-title-main">Dietary fiber</span> Portion of plant-derived food that cannot be completely digested

Dietary fiber or roughage is the portion of plant-derived food that cannot be completely broken down by human digestive enzymes. Dietary fibers are diverse in chemical composition and can be grouped generally by their solubility, viscosity and fermentability which affect how fibers are processed in the body. Dietary fiber has two main subtypes: soluble fiber and insoluble fiber which are components of plant-based foods such as legumes, whole grains, cereals, vegetables, fruits, and nuts or seeds. A diet high in regular fiber consumption is generally associated with supporting health and lowering the risk of several diseases. Dietary fiber consists of non-starch polysaccharides and other plant components such as cellulose, resistant starch, resistant dextrins, inulins, lignins, chitins, pectins, beta-glucans, and oligosaccharides.

<span class="mw-page-title-main">Mochi</span> Japanese rice cake

A mochi is a Japanese rice cake made of mochigome (もち米), a short-grain japonica glutinous rice, and sometimes other ingredients such as water, sugar, and cornstarch. The steamed rice is pounded into paste and molded into the desired shape. In Japan, it is traditionally made in a ceremony called mochitsuki. While eaten year-round, mochi is a traditional food for the Japanese New Year, and is commonly sold and eaten during that time.

<span class="mw-page-title-main">Maltose</span> Chemical compound

Maltose, also known as maltobiose or malt sugar, is a disaccharide formed from two units of glucose joined with an α(1→4) bond. In the isomer isomaltose, the two glucose molecules are joined with an α(1→6) bond. Maltose is the two-unit member of the amylose homologous series, the key structural motif of starch. When beta-amylase breaks down starch, it removes two glucose units at a time, producing maltose. An example of this reaction is found in germinating seeds, which is why it was named after malt. Unlike sucrose, it is a reducing sugar.

<span class="mw-page-title-main">Dextrin</span> Group of low-molecular-weight carbohydrates

Dextrins are a group of low-molecular-weight carbohydrates produced by the hydrolysis of starch and glycogen. Dextrins are mixtures of polymers of D-glucose units linked by α-(1→4) or α-(1→6) glycosidic bonds.

<span class="mw-page-title-main">Amylopectin</span> Chemical compound

Amylopectin is a water-insoluble polysaccharide and highly branched polymer of α-glucose units found in plants. It is one of the two components of starch, the other being amylose.

In cell biology, a granule is a small particle barely visible by light microscopy. The term is most often used to describe a secretory vesicle containing important components of cell physiology. Examples of granules include granulocytes, platelet granules, insulin granules, germane granules, starch granules, and stress granules.

<span class="mw-page-title-main">Cyclodextrin</span> Polysaccharide with six glucose units

Cyclodextrins are a family of cyclic oligosaccharides, consisting of a macrocyclic ring of glucose subunits joined by α-1,4 glycosidic bonds. Cyclodextrins are produced from starch by enzymatic conversion. They are used in food, pharmaceutical, drug delivery, and chemical industries, as well as agriculture and environmental engineering.

<span class="mw-page-title-main">Starch gelatinization</span> Process of breaking down the intermolecular bonds of starch by water

Starch gelatinization is a process of breaking down of intermolecular bonds of starch molecules in the presence of water and heat, allowing the hydrogen bonding sites to engage more water. This irreversibly dissolves the starch granule in water. Water acts as a plasticizer.

<span class="mw-page-title-main">Cycloamylose</span>

Cycloamyloses are cyclic α-1,4 linked glucans comprising dozens or hundreds of glucose units. Chemically they are similar to the much smaller cyclodextrins, which are typically composed of 6, 7 or 8 glucose units.

<span class="mw-page-title-main">Resistant starch</span> Dietary fiber

Resistant starch (RS) is starch, including its degradation products, that escapes from digestion in the small intestine of healthy individuals. Resistant starch occurs naturally in foods, but it can also be added as part of dried raw foods, or used as an additive in manufactured foods.

<span class="mw-page-title-main">Waxy corn</span> Type of field corn

Waxy corn or glutinous corn is a type of field corn characterized by its sticky texture when cooked as a result of larger amounts of amylopectin. The corn was first described from a specimen from China in 1909. As this plant showed many peculiar traits, the American breeders long used it as a genetic marker to tag the existence of hidden genes in other maize breeding programs. In 1922 a researcher found that the endosperm of waxy maize contained only amylopectin and no amylose starch molecule in opposition to normal dent corn varieties that contain both. Until World War II, the main source of starch in the United States was tapioca, but when Japan severed the supply lines of the U.S., they forced processors to turn to waxy maize. Amylopectin or waxy starch is now used mainly in food products, but also in the textile, adhesive, corrugating and paper industry.

A glucan is a polysaccharide derived from D-glucose, linked by glycosidic bonds. Glucans are noted in two forms: alpha glucans and beta glucans. Many beta-glucans are medically important. They represent a drug target for antifungal medications of the echinocandin class.

<span class="mw-page-title-main">Starch synthase</span> Enzyme family

In enzymology, a starch synthase is an enzyme that catalyzes the chemical reaction

Retrogradation is a reaction that takes place when the amylose and amylopectin chains in cooked, gelatinized starch realign themselves as the cooked starch cools.

Carbohydrate synthesis is a sub-field of organic chemistry concerned with generating complex carbohydrate structures from simple units (monosaccharides). The generation of carbohydrate structures usually involves linking monosaccharides or oligosaccharides through glycosidic bonds, a process called glycosylation. Therefore, it is important to construct glycosidic linkages that have optimum molecular geometry (stereoselectivity) and the stable bond (regioselectivity) at the reaction site.

<span class="mw-page-title-main">Alpha glucan</span>

α-Glucans (alpha-glucans) are polysaccharides of D-glucose monomers linked with glycosidic bonds of the alpha form. α-Glucans use cofactors in a cofactor site in order to activate a glucan phosphorylase enzyme. This enzyme causes a reaction that transfers a glucosyl portion between orthophosphate and α-I,4-glucan. The position of the cofactors to the active sites on the enzyme are critical to the overall reaction rate thus, any alteration to the cofactor site leads to the disruption of the glucan binding site.

<span class="mw-page-title-main">Floridean starch</span> Type of storage glucan

Floridean starch is a type of a storage glucan found in glaucophytes and in red algae, in which it is usually the primary sink for fixed carbon from photosynthesis. It is found in grains or granules in the cell's cytoplasm and is composed of an α-linked glucose polymer with a degree of branching intermediate between amylopectin and glycogen, though more similar to the former. The polymers that make up floridean starch are sometimes referred to as "semi-amylopectin".

References

  1. Green, Mark M.; Blankenhorn, Glenn; Hart, Harold (November 1975). "Which Starch Fraction is Water-Soluble, Amylose or Amylopectin?". Journal of Chemical Education. 52 (11): 729. Bibcode:1975JChEd..52..729G. doi:10.1021/ed052p729. ... amylose is the water-insoluble starch component.
  2. "Resistant starch". Archived from the original on 2010-09-24. Retrieved 2010-07-02.
  3. Nelson, David and Michael M. Cox. Principles of Biochemistry. 5th ed. New York: W. H. Freeman and Company, 2008.[ page needed ]
  4. a visualisation with references to the literature is found here
  5. Cohen, R.; Orlova, Y.; Kovalev, M.; Ungar, Y.; Shimoni, E. (2008). "Structural and Functional Properties of Amylose Complexes with Genistein". Journal of Agricultural and Food Chemistry. 56 (11): 4212–4218. doi:10.1021/jf800255c. PMID   18489110.
  6. 1 2 "Starch". Archived from the original on 2012-01-14. Retrieved 2010-05-25.
  7. Sarko, A; Wu, H.-C. H (1978). "The Crystal Structures of A-, B- and C-Polymorphs of Amylose and Starch". Starch - Stärke. 30 (3): 73–78. doi:10.1002/star.19780300302.
  8. Birt DF, Boylston T, Hendrich S, Jane JL, Hollis J, Li L, McClelland J, Moore S, Phillips GJ, Rowling M, Schalinske K, Scott MP, Whitley EM (2013). "Resistant starch: promise for improving human health". Advances in Nutrition . 4 (6): 587–601. doi:10.3945/an.113.004325. PMC   3823506 . PMID   24228189.
  9. "Which Starch Fraction is Water-Soluble, Amylose or Amylopectin?". A survey of 22 popular organic chemistry textbooks showed that only four correctly stated that of the two components of starch, amylopectin is the water-soluble, and amylose is the water-insoluble.
  10. Green, Mark M; Blankenhorn, Glenn; Hart, Harold (1975). "Which starch fraction is water-soluble, amylose or amylopectin?". Journal of Chemical Education. 52 (11): 729. Bibcode:1975JChEd..52..729G. doi:10.1021/ed052p729.
  11. Li, Jeng-Yune; Yeh, An-I (2001). "Relationships between thermal, rheological characteristics and swelling power for various starches" (PDF). Journal of Food Engineering. 50 (3): 141–148. doi:10.1016/S0260-8774(00)00236-3. Archived from the original (PDF) on 2022-09-21. Retrieved 2021-11-16.
  12. Pycia, K; Gałkowska, D; Juszczak, L; Fortuna, T; Witczak, T (2014). "Physicochemical, thermal and rheological properties of starches isolated from malting barley varieties". Journal of Food Science and Technology. 52 (8): 4797–4807. doi:10.1007/s13197-014-1531-3. PMC   4519444 . PMID   26243900.
  13. Wang, Juan; Hu, Pan; Chen, Zichun; Liu, Qiaoquan; Wei, Cunxu (2017). "Progress in High-Amylose Cereal Crops through Inactivation of Starch Branching Enzymes". Frontiers in Plant Science. 8: 469. doi: 10.3389/fpls.2017.00469 . PMC   5379859 . PMID   28421099.
  14. Chung, Hyun-Jung; Liu, Qiang (2009). "Impact of molecular structure of amylopectin and amylose on amylose chain association during cooling". Carbohydrate Polymers. 77 (4): 807–815. doi:10.1016/j.carbpol.2009.03.004.
  15. Wolff, Ivan A.; Davis, H. A.; Cluskey, J. E.; Gundrum, L. J.; Rist, Carl E. (April 1951). "Preparation of Films from Amylose". Industrial & Engineering Chemistry. 43 (4): 915–919. doi:10.1021/ie50496a039.
  16. Rindlav-Westling, A˚sa; Stading, Mats; Hermansson, Anne-Marie; Gatenholm, Paul (July 1998). "Structure, mechanical and barrier properties of amylose and amylopectin films". Carbohydrate Polymers. 36 (2–3): 217–224. doi:10.1016/S0144-8617(98)00025-3.
  17. Myllärinen, Päivi; Partanen, Riitta; Seppälä, Jukka; Forssell, Pirkko (December 2002). "Effect of glycerol on behaviour of amylose and amylopectin films". Carbohydrate Polymers. 50 (4): 355–361. doi:10.1016/S0144-8617(02)00042-5.
  18. "Biochemistry Structure and Function". Archived from the original on 2011-09-27. Retrieved 2010-05-25.
  19. "Amylose Magnetic Beads(E8035), pMAL Companion Products, NEB". Archived from the original on 2010-01-08. Retrieved 2010-05-25.
  20. Juliano, B. O.; Perez, C. M.; Komindr, S.; Banphotkasem, S. (December 1989). "Properties of Thai cooked rice and noodles differing in glycemic index in noninsulin-dependent diabetics". Plant Foods for Human Nutrition (Dordrecht, Netherlands). 39 (4): 369–374. doi:10.1007/bf01092074. ISSN   0921-9668. PMID   2631091. S2CID   189939655.
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  22. Seung, David; Soyk, Sebastian; Coiro, Mario; Maier, Benjamin A; Eicke, Simona; Zeeman, Samuel C (2015). "PROTEIN TARGETING TO STARCH is Required for Localising GRANULE-BOUND STARCH SYNTHASE to Starch Granules and for Normal Amylose Synthesis in Arabidopsis". PLOS Biology. 13 (2): e1002080. doi: 10.1371/journal.pbio.1002080 . PMC   4339375 . PMID   25710501.