1,4-alpha-D-glucan (PAMDB001519)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB001519
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
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
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
Average Molecular Weight: Not Available
Monoisotopic Molecular Weight: 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
Taxonomy DescriptionThis compound 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 ClassOrganooxygen compounds
Class Carbohydrates and carbohydrate conjugates
Sub ClassGlycosyl compounds
Direct Parent O-glycosyl compounds
Alternative Parents
Substituents
  • O-glycosyl compound
  • Disaccharide
  • Oxane
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Dialkyl ether
  • Acetal
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular Framework Aliphatic heteromonocyclic compounds
External Descriptors Not Available
Physical Properties
State: Solid
Charge:Not Available
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
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
Pathways: Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
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
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
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

Protein Details
• 1,4-alpha-glucan-branching enzyme
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
Locus Tag:
PA2153
Molecular weight:
82.6 kDa
Reactions
Transfers a segment of a (1->4)-alpha-D-glucan chain to a primary hydroxy group in a similar glucan chain.
Protein Details
• Glycogen phosphorylase
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
Locus Tag:
PA2144
Molecular weight:
92 kDa
Reactions
(1,4-alpha-D-glucosyl)(n) + phosphate = (1,4-alpha-D-glucosyl)(n-1) + alpha-D-glucose 1-phosphate.
Protein Details
• Maltose/maltodextrin import ATP-binding protein MalK
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
Locus Tag:
PA2341
Molecular weight:
40.2 kDa
Reactions
ATP + H(2)O + maltose(Out) = ADP + phosphate + maltose(In).

Transporters

Protein Details
• Maltose/maltodextrin import ATP-binding protein MalK
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
Locus Tag:
PA2341
Molecular weight:
40.2 kDa
Reactions
ATP + H(2)O + maltose(Out) = ADP + phosphate + maltose(In).