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Record Information
Version3.6
Creation Date2006-08-12 20:13:38 UTC
Update Date2013-05-29 19:38:10 UTC
HMDB IDHMDB03403
Secondary Accession NumbersNone
Metabolite Identification
Common NameAmylose
DescriptionAmylose 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 ).
Structure
Thumb
Synonyms
  1. (1,4-alpha-D-Glucosyl)N
  2. (1,4-alpha-D-Glucosyl)N+1
  3. (1,4-alpha-D-Glucosyl)N-1
  4. (1,4-alpha-delta-Glucosyl)N
  5. (1,4-alpha-delta-Glucosyl)N+1
  6. (1,4-alpha-delta-Glucosyl)N-1
  7. 1,4-alpha-D-Glucan
  8. 1,4-alpha-delta-Glucan
  9. 4-{(1,4)-alpha-D-Glucosyl}(N-1)-D-glucose
  10. 4-{(1,4)-alpha-delta-Glucosyl}(N-1)-delta-glucose
  11. Amylose
  12. Amylose chain
Chemical FormulaNot Available
Average Molecular WeightNot Available
Monoisotopic Molecular WeightNot Available
IUPAC NameNot Available
Traditional IUPAC NameNot Available
CAS Registry Number9005-82-7
SMILES
InChI Identifier
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
InChI KeyPTHCMJGKKRQCBF-OLYDTGNASA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassCarbohydrates and Carbohydrate Conjugates
ClassDisaccharides
Sub ClassDihexoses
Other Descriptors
  • Aliphatic Heteropolycyclic Compounds
Substituents
  • 1,2 Diol
  • Acetal
  • Dialkyl Ether
  • Glycosyl Compound
  • O Glycosyl Compound
  • Oxane
  • Primary Alcohol
  • Secondary Alcohol
Direct ParentDihexoses
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Spectra
SpectraMS/MS1D NMR2D NMR
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Starch and Sucrose MetabolismSMP00058map00500
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB001130
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC00718
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAmylose
NuGOwiki LinkHMDB03403
Metagene LinkHMDB03403
METLIN ID6917
PubChem Compound53477771
PDB IDNot Available
ChEBI ID28102
References
Synthesis ReferenceBreitinger, 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)
General References
  1. 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
  2. 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
  3. 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
  4. Traub WH: Studies on neutralization of human serum bactericidal activity by sodium amylosulfate. J Clin Microbiol. 1977 Aug;6(2):128-31. Pubmed: 330560
  5. Buleon A, Colonna P, Planchot V, Ball S: Starch granules: structure and biosynthesis. Int J Biol Macromol. 1998 Aug;23(2):85-112. Pubmed: 9730163

Enzymes

General function:
Involved in catalytic activity
Specific function:
Multifunctional enzyme acting as 1,4-alpha-D-glucan:1,4-alpha-D-glucan 4-alpha-D-glycosyltransferase and amylo-1,6-glucosidase in glycogen degradation.
Gene Name:
AGL
Uniprot ID:
P35573
Molecular weight:
Not Available
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:
PYGL
Uniprot ID:
P06737
Molecular weight:
93133.25
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:
PYGM
Uniprot ID:
P11217
Molecular weight:
87316.355
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:
PYGB
Uniprot ID:
P11216
Molecular weight:
96695.18
General function:
Involved in glycogen (starch) synthase activity
Specific function:
Transfers the glycosyl residue from UDP-Glc to the non-reducing end of alpha-1,4-glucan.
Gene Name:
GYS2
Uniprot ID:
P54840
Molecular weight:
80988.42
General function:
Involved in glycogen (starch) synthase activity
Specific function:
Transfers the glycosyl residue from UDP-Glc to the non-reducing end of alpha-1,4-glucan.
Gene Name:
GYS1
Uniprot ID:
P13807
Molecular weight:
76482.48
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
Not Available
Uniprot ID:
Q59ET0
Molecular weight:
86112.7