<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>2.0</version>
  <creation_date>2012-07-30 14:54:39 -0600</creation_date>
  <update_date>2015-09-17 16:24:30 -0600</update_date>
  <accession>ECMDB21110</accession>
  <m2m_id>M2MDB001519</m2m_id>
  <name>1,4-alpha-D-glucan</name>
  <description>Amylose is a linear polymer made up of D-glucose units.; Amylose is defined as a linear molecule of (1&amp;#8594;4) linked alpha-D-glucopyranosyl units, but it is today well established that some molecules are slightly branched by (1&amp;#8594;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&amp;#8594;4) bonds from the non-reducing end of a chain releasing beta-maltosyl units, but cannot cleave the (1&amp;#8594;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.</description>
  <synonyms>
    <synonym>(1,4-a-D-Glucosyl)N</synonym>
    <synonym>(1,4-a-D-Glucosyl)n+1</synonym>
    <synonym>(1,4-a-D-Glucosyl)N-1</synonym>
    <synonym>(1,4-a-delta-Glucosyl)N</synonym>
    <synonym>(1,4-a-delta-Glucosyl)n+1</synonym>
    <synonym>(1,4-a-delta-Glucosyl)N-1</synonym>
    <synonym>(1,4-a-δ-Glucosyl)N</synonym>
    <synonym>(1,4-a-δ-Glucosyl)n+1</synonym>
    <synonym>(1,4-a-δ-Glucosyl)N-1</synonym>
    <synonym>(1,4-alpha-D-Glucosyl)N</synonym>
    <synonym>(1,4-alpha-D-Glucosyl)N+1</synonym>
    <synonym>(1,4-alpha-D-Glucosyl)N-1</synonym>
    <synonym>(1,4-alpha-delta-Glucosyl)N</synonym>
    <synonym>(1,4-alpha-delta-Glucosyl)N+1</synonym>
    <synonym>(1,4-alpha-delta-Glucosyl)N-1</synonym>
    <synonym>(1,4-α-D-Glucosyl)N</synonym>
    <synonym>(1,4-α-D-Glucosyl)n+1</synonym>
    <synonym>(1,4-α-D-Glucosyl)N-1</synonym>
    <synonym>(1,4-α-δ-Glucosyl)N</synonym>
    <synonym>(1,4-α-δ-Glucosyl)n+1</synonym>
    <synonym>(1,4-α-δ-Glucosyl)N-1</synonym>
    <synonym>1,4-a-D-Glucan</synonym>
    <synonym>1,4-a-delta-Glucan</synonym>
    <synonym>1,4-a-δ-Glucan</synonym>
    <synonym>1,4-alpha-D-Glucan</synonym>
    <synonym>1,4-alpha-delta-Glucan</synonym>
    <synonym>1,4-α-D-Glucan</synonym>
    <synonym>1,4-α-δ-Glucan</synonym>
    <synonym>4-{(1,4)-a-D-glucosyl}(N-1)-D-glucose</synonym>
    <synonym>4-{(1,4)-a-delta-glucosyl}(N-1)-delta-glucose</synonym>
    <synonym>4-{(1,4)-a-δ-glucosyl}(N-1)-δ-glucose</synonym>
    <synonym>4-{(1,4)-alpha-D-Glucosyl}(N-1)-D-glucose</synonym>
    <synonym>4-{(1,4)-alpha-delta-Glucosyl}(N-1)-delta-glucose</synonym>
    <synonym>4-{(1,4)-α-D-glucosyl}(N-1)-D-glucose</synonym>
    <synonym>4-{(1,4)-α-δ-glucosyl}(N-1)-δ-glucose</synonym>
    <synonym>Amylose</synonym>
    <synonym>Amylose chain</synonym>
    <synonym>Maltodextrin (NF)</synonym>
  </synonyms>
  <chemical_formula>(C12H20O11)nC2H6</chemical_formula>
  <average_molecular_weight/>
  <monisotopic_moleculate_weight/>
  <iupac_name/>
  <traditional_iupac/>
  <cas_registry_number>9005-82-7</cas_registry_number>
  <smiles/>
  <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</inchi>
  <inchikey>PTHCMJGKKRQCBF-OLYDTGNASA-N</inchikey>
  <state>Solid</state>
  <cellular_locations>
    <cellular_location>Cytosol</cellular_location>
    <cellular_location>Extra-organism</cellular_location>
    <cellular_location>Periplasm</cellular_location>
  </cellular_locations>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.41</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.04</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>3.39e+02 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>formula</kind>
    <value>(C12H20O11)nC2H6</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>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</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>PTHCMJGKKRQCBF-OLYDTGNASA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formal_charge</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>72540</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1995</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1961</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>21622</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>21623</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>21624</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>21625</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>21626</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>21627</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>21628</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>21629</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>21630</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>21631</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>21632</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>21633</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>21634</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>21635</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>21636</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>21637</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>21638</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>21639</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>21640</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>21641</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2280</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2281</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2282</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1218415</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1218416</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1218417</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2781547</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2781548</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2781549</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2926936</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2926937</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2926938</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1895</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB03403</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id>C00718</kegg_id>
  <chebi_id>15444</chebi_id>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <foodb_id/>
  <general_references>
    <reference>
      <reference_text>Buleon, A., Colonna, P., Planchot, V., Ball, S. (1998). "Starch granules: structure and biosynthesis." Int J Biol Macromol 23:85-112.</reference_text>
      <pubmed_id>9730163</pubmed_id>
    </reference>
    <reference>
      <reference_text>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.</reference_text>
      <pubmed_id>9109613</pubmed_id>
    </reference>
    <reference>
      <reference_text>Klein B, Foreman JA: Amylolysis of a chromogenic substrate, Cibachron Blue F3GA-amylose: kinetics and mechanism. Clin Chem. 1980 Feb;26(2):250-3.</reference_text>
      <pubmed_id>6153298</pubmed_id>
    </reference>
    <reference>
      <reference_text>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.</reference_text>
      <pubmed_id>9846590</pubmed_id>
    </reference>
    <reference>
      <reference_text>Traub WH: Studies on neutralization of human serum bactericidal activity by sodium amylosulfate. J Clin Microbiol. 1977 Aug;6(2):128-31.</reference_text>
      <pubmed_id>330560</pubmed_id>
    </reference>
  </general_references>
  <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.</synthesis_reference>
  <msds_url>http://hmdb.ca/system/metabolites/msds/000/002/984/original/HMDB03403.pdf?1358893427</msds_url>
  <enzymes>
    <enzyme>
      <name>Maltodextrin phosphorylase</name>
      <uniprot_id>P00490</uniprot_id>
      <uniprot_name>PHSM_ECOLI</uniprot_name>
      <gene_name>malP</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P00490.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>1,4-alpha-glucan-branching enzyme</name>
      <uniprot_id>P07762</uniprot_id>
      <uniprot_name>GLGB_ECOLI</uniprot_name>
      <gene_name>glgB</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P07762.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>Glycogen synthase</name>
      <uniprot_id>P0A6U8</uniprot_id>
      <uniprot_name>GLGA_ECOLI</uniprot_name>
      <gene_name>glgA</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P0A6U8.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>Glycogen phosphorylase</name>
      <uniprot_id>P0AC86</uniprot_id>
      <uniprot_name>PHSG_ECOLI</uniprot_name>
      <gene_name>glgP</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P0AC86.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>4-alpha-glucanotransferase</name>
      <uniprot_id>P15977</uniprot_id>
      <uniprot_name>MALQ_ECOLI</uniprot_name>
      <gene_name>malQ</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P15977.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>Alpha-amylase</name>
      <uniprot_id>P25718</uniprot_id>
      <uniprot_name>AMY1_ECOLI</uniprot_name>
      <gene_name>malS</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P25718.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>Cytoplasmic alpha-amylase</name>
      <uniprot_id>P26612</uniprot_id>
      <uniprot_name>AMY2_ECOLI</uniprot_name>
      <gene_name>amyA</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P26612.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>Maltose/maltodextrin import ATP-binding protein MalK</name>
      <uniprot_id>P68187</uniprot_id>
      <uniprot_name>MALK_ECOLI</uniprot_name>
      <gene_name>malK</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P68187.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>Maltose transport system permease protein malF</name>
      <uniprot_id>P02916</uniprot_id>
      <uniprot_name>MALF_ECOLI</uniprot_name>
      <gene_name>malF</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P02916.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>Maltose transport system permease protein malG</name>
      <uniprot_id>P68183</uniprot_id>
      <uniprot_name>MALG_ECOLI</uniprot_name>
      <gene_name>malG</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P68183.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>Maltose-binding periplasmic protein</name>
      <uniprot_id>P0AEX9</uniprot_id>
      <uniprot_name>MALE_ECOLI</uniprot_name>
      <gene_name>malE</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P0AEX9.xml</protein_url>
    </enzyme>
  </enzymes>
  <transporters>
    <enzyme>
      <name>Maltose/maltodextrin import ATP-binding protein MalK</name>
      <uniprot_id>P68187</uniprot_id>
      <uniprot_name>MALK_ECOLI</uniprot_name>
      <gene_name>malK</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P68187.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>Maltose transport system permease protein malF</name>
      <uniprot_id>P02916</uniprot_id>
      <uniprot_name>MALF_ECOLI</uniprot_name>
      <gene_name>malF</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P02916.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>Maltose transport system permease protein malG</name>
      <uniprot_id>P68183</uniprot_id>
      <uniprot_name>MALG_ECOLI</uniprot_name>
      <gene_name>malG</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P68183.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>Maltose-binding periplasmic protein</name>
      <uniprot_id>P0AEX9</uniprot_id>
      <uniprot_name>MALE_ECOLI</uniprot_name>
      <gene_name>malE</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P0AEX9.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>Maltoporin</name>
      <uniprot_id>P02943</uniprot_id>
      <uniprot_name>LAMB_ECOLI</uniprot_name>
      <gene_name>lamB</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P02943.xml</protein_url>
    </enzyme>
  </transporters>
  <reactions>
    <reaction_text>Adenosine triphosphate + Water + 1,4-alpha-D-glucan &gt; 1,4-alpha-D-glucan + ADP + Hydrogen ion + Phosphate</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>Adenosine triphosphate + Water + 1,4-alpha-D-glucan &gt; 1,4-alpha-D-glucan + ADP + Hydrogen ion + Phosphate</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>1,4-alpha-D-glucan &gt; Maltohexaose</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>1,4-alpha-D-glucan &lt;&gt; Starch</reaction_text>
    <kegg_reaction_id>R02110</kegg_reaction_id>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>Starch + Phosphate &lt;&gt; 1,4-alpha-D-glucan + Glucose 1-phosphate</reaction_text>
    <kegg_reaction_id>R02111</kegg_reaction_id>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>ADP-Glucose + 1,4-alpha-D-glucan &lt;&gt; ADP + 1,4-alpha-D-glucan</reaction_text>
    <kegg_reaction_id>R02421</kegg_reaction_id>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>ADP-Glucose + 1,4-alpha-D-glucan &lt;&gt; ADP + 1,4-alpha-D-glucan</reaction_text>
    <kegg_reaction_id>R02421</kegg_reaction_id>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>1,4-alpha-D-glucan + D-Glucose &lt;&gt; D-Maltose</reaction_text>
    <kegg_reaction_id>R05196</kegg_reaction_id>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>Starch + Phosphate &lt;&gt; 1,4-alpha-D-glucan + Glucose 1-phosphate</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>1,4-alpha-D-glucan &lt;&gt; Starch</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>Starch + Phosphate &lt;&gt; 1,4-alpha-D-glucan + Glucose 1-phosphate</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>1,4-alpha-D-glucan &lt;&gt; Starch</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id/>
    <pw_reaction_id/>
  </reactions>
  <concentrations>
  </concentrations>
</compound>
