N-Acetyl-D-Glucosamine → HCID 131725372, compound

HRID 891982Notes

Reaction equation

HRID 891982 reaction equation
[C:1]([NH:4][C@@H:5]1[C@@H:11]([OH:12])[C@H:10]([OH:13])[C@@H:9]([CH2:14][OH:15])[O:8][CH:6]1[OH:7])(=[O:3])[CH3:2].[O:16]([C@@H:28]1[C@@H:81]([CH2:82][OH:83])[O:80][C@@H:31]([O:32][C@H:33]2[C@@H:75]([OH:76])[C@@H:74]([CH2:77][OH:78])[O:73][C@@H:35](O[C@@H]3[C@@H](CO)O[C@@H](O[C@H]4[C@@H](O)[C@@H](CO)O[C@@H](O[C@@H]5[C@@H](CO)OC(O)[C@H](O)[C@H]5O)[C@@H]4O)[C@H](NC(C)=O)[C@H]3O)[C@@H:34]2[OH:79])[C@H:30]([NH:84][C:85]([CH3:87])=[O:86])[C@H:29]1[OH:88])[C@@H:17]1[O:25][C@H:24]([CH2:26][OH:27])[C@H:22]([OH:23])[C@H:20]([OH:21])[C@H:18]1[OH:19].CC(N[C@H]1[C@H](O[C@@H]2[C@@H](O)[C@H](O[C@H]3[C@H](O)[C@@H](O)C(O)O[C@@H]3CO)O[C@H](CO)[C@@H]2O)O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@@H]1O)=O.[CH3:137][CH:138]1[O:143][CH:142]([O:144][CH:145]([CH:150]([O:155][CH:156]2[O:161][CH:160]([CH2:162][OH:163])[CH:159]([OH:164])[CH:158](OC3OC(CO)C(O)C(OC4OC(CO)C(O)C(O)C4O)C3NC(C)=O)[CH:157]2[OH:191])[CH:151]([OH:154])[CH2:152][OH:153])[CH:146]([OH:149])[CH:147]=[O:148])[CH:141]([OH:192])[CH:140]([OH:193])[CH:139]1[OH:194].O([C@H]1[C@H](O)[C@@H](CO)O[C@@H](O[C@H]2[C@@H](O)[C@@H](CO)O[C@@H](O[C@@H]3[C@@H](CO)OC(O)[C@H](O)[C@H]3O[C@@H]3O[C@@H](C)[C@@H](O)[C@@H](O)[C@@H]3O)[C@@H]2O)[C@@H]1NC(C)=O)[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O>>[O:16]([C@@H:28]1[C@@H:81]([CH2:82][OH:83])[O:80][C@@H:31]([O:32][C@H:33]2[C@@H:75]([OH:76])[C@@H:74]([CH2:77][OH:78])[O:73][C@@H:35]([O:12][C@H:11]3[C@H:10]([OH:13])[C@@H:9]([CH2:14][OH:15])[O:8][C@@H:6]([O:7][C@H:158]4[C@@H:159]([OH:164])[C@@H:160]([CH2:162][OH:163])[O:161][C@@H:156]([O:155][C@@H:150]5[C@@H:151]([CH2:152][OH:153])[O:154][CH:147]([OH:148])[C@H:146]([OH:149])[C@H:145]5[O:144][C@@H:142]5[O:143][C@@H:138]([CH3:137])[C@@H:139]([OH:194])[C@@H:140]([OH:193])[C@@H:141]5[OH:192])[C@@H:157]4[OH:191])[C@@H:5]3[NH:4][C:1]([CH3:2])=[O:3])[C@@H:34]2[OH:79])[C@H:30]([NH:84][C:85]([CH3:87])=[O:86])[C@H:29]1[OH:88])[C@@H:17]1[O:25][C@H:24]([CH2:26][OH:27])[C@H:22]([OH:23])[C@H:20]([OH:21])[C@H:18]1[OH:19]

Participants

6

Reactant 5

HCID 439174N-Acetyl-D-GlucosamineHCID 4096542HCID 4096542, compoundHCID 9831622HCID 9831622, compoundHCID 11240191HCID 11240191, compoundHCID 91849566HCID 91849566, compound

Product 1

HCID 131725372HCID 131725372, compound

Procedure

A sugar chain in which N-acetylglucosamine was added to the non-reducing end of the sugar chain (Galβ1-4GlcNAcβ1-3Galβ1-4GlcNAcβ1-3Galβ1-4Glc) was synthesized by allowing the FLAG peptide-fused G4 polypeptide produced as a secreted form in Example 10 to react simultaneously with LNnT and β1,4-galactosyltransferase (manufactured by SIGMA) purified from bovine milk. In the same manner, Galβ1-4GlcNAcβ1-3Galβ1-3GlcNAcβ1-3Galβ1-4Glc was synthesized using LNT as a substrate. Also, Galβ1-4GlcNAcβ1-3Galβ1-3GlcNAcβ1-3Galβ1-4(Fucα1-3)Glc was synthesized by using LNFP-V [(Galβ1-3GlcNAcβ1-3Galβ1-4(Fucα1-3)Glc) as a substrate. The specific reaction was carried out as follows.

Workup

  1. customwas synthesized
  2. customproduced as a secreted form in Example 10
  3. custompurified from bovine milk
  4. customIn the same manner, Galβ1-4GlcNAcβ1-3Galβ1-3GlcNAcβ1-3Galβ1-4Glc was synthesized
  5. customThe specific reaction

Sources & evidence

ORD record
ord-10c9037bc0314be9952ae4dbb5aff82b
Source dataset
uspto-grants-2006_02
Patent number
US07005279B1

Reaction notes

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