
1,4-alpha-D-glucan (ECMDB21110) (M2MDB001519)
Record Information | |||||||||||||||||||
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Version | 2.0 | ||||||||||||||||||
Creation Date | 2012-07-30 14:54:39 -0600 | ||||||||||||||||||
Update Date | 2015-09-17 16:24:30 -0600 | ||||||||||||||||||
Secondary Accession Numbers |
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Identification | |||||||||||||||||||
Name: | 1,4-alpha-D-glucan | ||||||||||||||||||
Description | Amylose is a linear polymer made up of D-glucose units.; Amylose is defined as a linear molecule of (1→4) linked alpha-D-glucopyranosyl units, but it is today well established that some molecules are slightly branched by (1→6)-alpha-linkages. ; The oldest criteria for linearity consisted in the susceptibility of the molecule to complete hydrolysis by beta-amylase. This enzyme splits the (1→4) bonds from the non-reducing end of a chain releasing beta-maltosyl units, but cannot cleave the (1→6) bonds. When degraded by pure beta-amylase, linear macromolecules are completely converted into maltose, whereas branched chains give also one beta-limit dextrin consisting of the remaining inner core polysaccharide structure with its outer chains recessed.; Starches of different botanical origins possess different granular sizes, morphology, polymorphism and enzyme digestibility. These characteristics are related to the chemical structures of the amylopectin and amylose and how they are arranged in the starch granule. (PMID 9730163); 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.; This polysaccharide is one of the two components of starch, making up approximately 20-30% of the structure. The other component is amylopectin, which makes up 70-80% of the structure. | ||||||||||||||||||
Structure | |||||||||||||||||||
Synonyms: |
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Chemical Formula: | (C12H20O11)nC2H6 | ||||||||||||||||||
Weight: | Average: Not Available Monoisotopic: Not Available | ||||||||||||||||||
InChI Key: | PTHCMJGKKRQCBF-OLYDTGNASA-N | ||||||||||||||||||
InChI: | InChI=1S/C14H26O11/c1-21-11-5(3-15)24-14(10(20)7(11)17)25-12-6(4-16)23-13(22-2)9(19)8(12)18/h5-20H,3-4H2,1-2H3/t5-,6-,7-,8-,9-,10-,11-,12-,13+,14-/m1/s1 | ||||||||||||||||||
CAS number: | 9005-82-7 | ||||||||||||||||||
IUPAC Name: | Not Available | ||||||||||||||||||
Traditional IUPAC Name: | Not Available | ||||||||||||||||||
SMILES: | Not Available | ||||||||||||||||||
Chemical Taxonomy | |||||||||||||||||||
Description | belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. | ||||||||||||||||||
Kingdom | Organic compounds | ||||||||||||||||||
Super Class | Organic oxygen compounds | ||||||||||||||||||
Class | Organooxygen compounds | ||||||||||||||||||
Sub Class | Carbohydrates and carbohydrate conjugates | ||||||||||||||||||
Direct Parent | O-glycosyl compounds | ||||||||||||||||||
Alternative Parents | |||||||||||||||||||
Substituents |
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Molecular Framework | Aliphatic heteromonocyclic compounds | ||||||||||||||||||
External Descriptors | Not Available | ||||||||||||||||||
Physical Properties | |||||||||||||||||||
State: | Solid | ||||||||||||||||||
Charge: | Not Available | ||||||||||||||||||
Melting point: | Not Available | ||||||||||||||||||
Experimental Properties: |
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Predicted Properties |
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Biological Properties | |||||||||||||||||||
Cellular Locations: | Cytoplasm | ||||||||||||||||||
Reactions: | Adenosine triphosphate + Water + 1,4-alpha-D-glucan > 1,4-alpha-D-glucan + ADP + Hydrogen ion + Phosphate Adenosine triphosphate + Water + 1,4-alpha-D-glucan > 1,4-alpha-D-glucan + ADP + Hydrogen ion + Phosphate 1,4-alpha-D-glucan > Maltohexaose 1,4-alpha-D-glucan <> Starch Starch + Phosphate <> 1,4-alpha-D-glucan + Glucose 1-phosphate ADP-Glucose + 1,4-alpha-D-glucan <> ADP + 1,4-alpha-D-glucan ADP-Glucose + 1,4-alpha-D-glucan <> ADP + 1,4-alpha-D-glucan 1,4-alpha-D-glucan + D-Glucose <> D-Maltose Starch + Phosphate <> 1,4-alpha-D-glucan + Glucose 1-phosphate 1,4-alpha-D-glucan <> Starch Starch + Phosphate <> 1,4-alpha-D-glucan + Glucose 1-phosphate 1,4-alpha-D-glucan <> Starch | ||||||||||||||||||
SMPDB Pathways: | Not Available | ||||||||||||||||||
KEGG Pathways: | Not Available | ||||||||||||||||||
EcoCyc Pathways: | Not Available | ||||||||||||||||||
Concentrations | |||||||||||||||||||
Not Available | |||||||||||||||||||
Spectra | |||||||||||||||||||
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References | |||||||||||||||||||
References: |
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Synthesis Reference: | Breitinger, Hans-Georg. Synthesis and characterization of 2,3-di-O-alkylated amyloses: Hydrophobic substitution destabilizes helical conformation. Biopolymers (2003), 69(3), 301-310. | ||||||||||||||||||
Material Safety Data Sheet (MSDS) | Download (PDF) | ||||||||||||||||||
Links | |||||||||||||||||||
External Links: |
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Enzymes
- General function:
- Involved in phosphorylase activity
- Specific function:
- Phosphorylase is an important allosteric enzyme in carbohydrate metabolism. Enzymes from different sources differ in their regulatory mechanisms and in their natural substrates. However, all known phosphorylases share catalytic and structural properties
- Gene Name:
- malP
- Uniprot ID:
- P00490
- Molecular weight:
- 90522
Reactions
(1,4-alpha-D-glucosyl)(n) + phosphate = (1,4-alpha-D-glucosyl)(n-1) + alpha-D-glucose 1-phosphate. |
- General function:
- Involved in 1,4-alpha-glucan branching enzyme activity
- Specific function:
- Catalyzes the formation of the alpha-1,6-glucosidic linkages in glycogen by scission of a 1,4-alpha-linked oligosaccharide from growing alpha-1,4-glucan chains and the subsequent attachment of the oligosaccharide to the alpha-1,6 position. Has a preference for transferring chains of 5 to 16 glucose units
- Gene Name:
- glgB
- Uniprot ID:
- P07762
- Molecular weight:
- 84336
Reactions
Transfers a segment of a (1->4)-alpha-D-glucan chain to a primary hydroxy group in a similar glucan chain. |
- General function:
- Involved in biosynthetic process
- Specific function:
- Synthesizes alpha-1,4-glucan chains using ADP-glucose
- Gene Name:
- glgA
- Uniprot ID:
- P0A6U8
- Molecular weight:
- 52822
Reactions
ADP-glucose + (1,4-alpha-D-glucosyl)(n) = ADP + (1,4-alpha-D-glucosyl)(n+1). |
- General function:
- Involved in phosphorylase activity
- Specific function:
- Phosphorylase is an important allosteric enzyme in carbohydrate metabolism. Enzymes from different sources differ in their regulatory mechanisms and in their natural substrates. However, all known phosphorylases share catalytic and structural properties
- Gene Name:
- glgP
- Uniprot ID:
- P0AC86
- Molecular weight:
- 93172
Reactions
(1,4-alpha-D-glucosyl)(n) + phosphate = (1,4-alpha-D-glucosyl)(n-1) + alpha-D-glucose 1-phosphate. |
- General function:
- Involved in 4-alpha-glucanotransferase activity
- Specific function:
- Transfers a segment of a (1->4)-alpha-D-glucan to a new position in an acceptor, which may be glucose or a (1->4)-alpha-D-glucan
- Gene Name:
- malQ
- Uniprot ID:
- P15977
- Molecular weight:
- 78503
Reactions
Transfers a segment of a (1->4)-alpha-D-glucan to a new position in an acceptor, which may be glucose or a (1->4)-alpha-D-glucan. |
- General function:
- Involved in catalytic activity
- Specific function:
- Since only maltooligosaccharides up to a chain length of 6 glucose units are actively transported through the cytoplasmic membrane via the membrane-bound complex of three proteins, malF, malG, and malK, longer maltooligosaccharides must first be degraded by the periplasmic alpha-amylase, the malS protein
- Gene Name:
- malS
- Uniprot ID:
- P25718
- Molecular weight:
- 75712
Reactions
Endohydrolysis of (1->4)-alpha-D-glucosidic linkages in polysaccharides containing three or more (1->4)-alpha-linked D-glucose units. |
- General function:
- Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
- Specific function:
- Endohydrolysis of (1->4)-alpha-D-glucosidic linkages in oligosaccharides and polysaccharides
- Gene Name:
- amyA
- Uniprot ID:
- P26612
- Molecular weight:
- 56639
Reactions
Endohydrolysis of (1->4)-alpha-D-glucosidic linkages in polysaccharides containing three or more (1->4)-alpha-linked D-glucose units. |
- General function:
- Involved in nucleotide binding
- Specific function:
- Part of the ABC transporter complex MalEFGK involved in maltose/maltodextrin import. Responsible for energy coupling to the transport system
- Gene Name:
- malK
- Uniprot ID:
- P68187
- Molecular weight:
- 40990
Reactions
ATP + H(2)O + maltose(Out) = ADP + phosphate + maltose(In). |
- General function:
- Involved in transporter activity
- Specific function:
- Part of the binding-protein-dependent transport system for maltose; probably responsible for the translocation of the substrate across the membrane
- Gene Name:
- malF
- Uniprot ID:
- P02916
- Molecular weight:
- 57013
- General function:
- Involved in transporter activity
- Specific function:
- Part of the binding-protein-dependent transport system for maltose; probably responsible for the translocation of the substrate across the membrane
- Gene Name:
- malG
- Uniprot ID:
- P68183
- Molecular weight:
- 32225
- General function:
- Involved in maltose transmembrane transporter activity
- Specific function:
- Involved in the high-affinity maltose membrane transport system malEFGK. Initial receptor for the active transport of and chemotaxis toward maltooligosaccharides
- Gene Name:
- malE
- Uniprot ID:
- P0AEX9
- Molecular weight:
- 43387
Transporters
- General function:
- Involved in nucleotide binding
- Specific function:
- Part of the ABC transporter complex MalEFGK involved in maltose/maltodextrin import. Responsible for energy coupling to the transport system
- Gene Name:
- malK
- Uniprot ID:
- P68187
- Molecular weight:
- 40990
Reactions
ATP + H(2)O + maltose(Out) = ADP + phosphate + maltose(In). |
- General function:
- Involved in transporter activity
- Specific function:
- Part of the binding-protein-dependent transport system for maltose; probably responsible for the translocation of the substrate across the membrane
- Gene Name:
- malF
- Uniprot ID:
- P02916
- Molecular weight:
- 57013
- General function:
- Involved in transporter activity
- Specific function:
- Part of the binding-protein-dependent transport system for maltose; probably responsible for the translocation of the substrate across the membrane
- Gene Name:
- malG
- Uniprot ID:
- P68183
- Molecular weight:
- 32225
- General function:
- Involved in maltose transmembrane transporter activity
- Specific function:
- Involved in the high-affinity maltose membrane transport system malEFGK. Initial receptor for the active transport of and chemotaxis toward maltooligosaccharides
- Gene Name:
- malE
- Uniprot ID:
- P0AEX9
- Molecular weight:
- 43387
- General function:
- Involved in porin activity
- Specific function:
- Involved in the transport of maltose and maltodextrins, indispensable for translocation of dextrins containing more than three glucosyl moieties. A hydrophobic path ("greasy slide") of aromatic residues serves to guide and select the sugars for transport through the channel. Also acts as a receptor for several bacteriophages including lambda
- Gene Name:
- lamB
- Uniprot ID:
- P02943
- Molecular weight:
- 49912