Record Information
Version2.0
Creation Date2012-07-30 14:54:39 -0600
Update Date2015-09-17 16:24:30 -0600
Secondary Accession Numbers
  • ECMDB21110
Identification
Name:1,4-alpha-D-glucan
DescriptionAmylose 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
Thumb
Synonyms:
  • (1,4-a-D-Glucosyl)N
  • (1,4-a-D-Glucosyl)n+1
  • (1,4-a-D-Glucosyl)N-1
  • (1,4-a-delta-Glucosyl)N
  • (1,4-a-delta-Glucosyl)n+1
  • (1,4-a-delta-Glucosyl)N-1
  • (1,4-a-δ-Glucosyl)N
  • (1,4-a-δ-Glucosyl)n+1
  • (1,4-a-δ-Glucosyl)N-1
  • (1,4-alpha-D-Glucosyl)N
  • (1,4-alpha-D-Glucosyl)N+1
  • (1,4-alpha-D-Glucosyl)N-1
  • (1,4-alpha-delta-Glucosyl)N
  • (1,4-alpha-delta-Glucosyl)N+1
  • (1,4-alpha-delta-Glucosyl)N-1
  • (1,4-α-D-Glucosyl)N
  • (1,4-α-D-Glucosyl)n+1
  • (1,4-α-D-Glucosyl)N-1
  • (1,4-α-δ-Glucosyl)N
  • (1,4-α-δ-Glucosyl)n+1
  • (1,4-α-δ-Glucosyl)N-1
  • 1,4-a-D-Glucan
  • 1,4-a-delta-Glucan
  • 1,4-a-δ-Glucan
  • 1,4-alpha-D-Glucan
  • 1,4-alpha-delta-Glucan
  • 1,4-α-D-Glucan
  • 1,4-α-δ-Glucan
  • 4-{(1,4)-a-D-glucosyl}(N-1)-D-glucose
  • 4-{(1,4)-a-delta-glucosyl}(N-1)-delta-glucose
  • 4-{(1,4)-a-δ-glucosyl}(N-1)-δ-glucose
  • 4-{(1,4)-alpha-D-Glucosyl}(N-1)-D-glucose
  • 4-{(1,4)-alpha-delta-Glucosyl}(N-1)-delta-glucose
  • 4-{(1,4)-α-D-glucosyl}(N-1)-D-glucose
  • 4-{(1,4)-α-δ-glucosyl}(N-1)-δ-glucose
  • Amylose
  • Amylose chain
  • Maltodextrin (NF)
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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentO-glycosyl compounds
Alternative Parents
Substituents
  • O-glycosyl compound
  • Disaccharide
  • Oxane
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Dialkyl ether
  • Acetal
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
State:Solid
Charge:Not Available
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility339 g/LALOGPS
logP-2.4ALOGPS
logS-0.04ALOGPS
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0k9i-3329000000-2b7bd69033e8a4fea64aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0udi-0900000000-5eb2b079a3b131ab742eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0fb9-9700000000-8631a9ae75f1a201adc7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004i-9000000000-9b80204fe6afbb2eaf15View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0900000000-865ff3c21e042be41194View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ea-1900000000-ff3096b7f2c9d1141b1fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-9100000000-c4b6f8b4217029a276d9View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0229-9000000000-3cd18e57966112492f50View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Buleon, A., Colonna, P., Planchot, V., Ball, S. (1998). "Starch granules: structure and biosynthesis." Int J Biol Macromol 23:85-112. Pubmed: 9730163
  • Klein B, Foreman JA: Amylolysis of a chromogenic substrate, Cibachron Blue F3GA-amylose: kinetics and mechanism. Clin Chem. 1980 Feb;26(2):250-3. Pubmed: 6153298
  • Langkilde AM, Ekwall H, Bjorck I, Asp NG, Andersson H: Retrograded high-amylose corn starch reduces cholic acid excretion from the small bowel in ileostomy subjects. Eur J Clin Nutr. 1998 Nov;52(11):790-5. Pubmed: 9846590
  • Topping DL, Gooden JM, Brown IL, Biebrick DA, McGrath L, Trimble RP, Choct M, Illman RJ: A high amylose (amylomaize) starch raises proximal large bowel starch and increases colon length in pigs. J Nutr. 1997 Apr;127(4):615-22. Pubmed: 9109613
  • Traub WH: Studies on neutralization of human serum bactericidal activity by sodium amylosulfate. J Clin Microbiol. 1977 Aug;6(2):128-31. Pubmed: 330560
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)
External Links:
ResourceLink
CHEBI ID15444
HMDB IDHMDB03403
Pubchem Compound ID53477771
Kegg IDC00718
ChemSpider IDNot Available
Wikipedia IDAmylose
BioCyc IDNot Available

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