N,N',N''-Triacetylchitotriose → N-Acetylchitohexaose

HRID 1381967Notes

Reaction equation

HRID 1381967 reaction equation
[C:1]([NH:4][C@@H:5]1[C@@H:11]([OH:12])[C@H:10](O)[C@@H:9]([CH2:14][OH:15])[O:8][CH:6]1O)(=[O:3])[CH3:2].[CH3:16][C:17]([NH:19][C@H:20]1[C@H:25]([O:26][C@@H:27]([C@H:32]([OH:40])[C@@H:33]([NH:36][C:37]([CH3:39])=[O:38])[CH:34]=[O:35])[C@H:28]([OH:31])[CH2:29][OH:30])[O:24][C@H:23]([CH2:41][OH:42])[C@@H:22]([OH:43])[C@@H:21]1[OH:44])=[O:18].[CH3:45][C:46]([NH:48][C@H:49]1[C@H:54]([O:55][C@H:56]2[C@H:61]([OH:62])[C@@H:60]([NH:63][C:64]([CH3:66])=[O:65])[C@H:59]([O:67][C@@H:68]([C@H:73]([OH:81])[C@@H:74]([NH:77][C:78]([CH3:80])=[O:79])[CH:75]=[O:76])[C@H:69]([OH:72])[CH2:70][OH:71])[O:58][C@@H:57]2[CH2:82][OH:83])[O:53][C@H:52]([CH2:84][OH:85])[C@@H:51]([OH:86])[C@@H:50]1[OH:87])=[O:47]>O>[CH3:16][C:17]([NH:19][C@H:20]1[C@H:25]([O:26][C@H:27]2[C@H:32]([OH:40])[C@@H:33]([NH:36][C:37]([CH3:39])=[O:38])[C@H:34]([O:35][C@H:10]3[C@H:11]([OH:12])[C@@H:5]([NH:4][C:1]([CH3:2])=[O:3])[C@H:6]([O:86][C@H:51]4[C@H:50]([OH:87])[C@@H:49]([NH:48][C:46]([CH3:45])=[O:47])[C@H:54]([O:55][C@H:56]5[C@H:61]([OH:62])[C@@H:60]([NH:63][C:64]([CH3:66])=[O:65])[C@H:59]([O:67][C@@H:68]([C@H:73]([OH:81])[C@@H:74]([NH:77][C:78]([CH3:80])=[O:79])[CH:75]=[O:76])[C@H:69]([OH:72])[CH2:70][OH:71])[O:58][C@@H:57]5[CH2:82][OH:83])[O:53][C@@H:52]4[CH2:84][OH:85])[O:8][C@@H:9]3[CH2:14][OH:15])[O:31][C@@H:28]2[CH2:29][OH:30])[O:24][C@H:23]([CH2:41][OH:42])[C@@H:22]([OH:43])[C@@H:21]1[OH:44])=[O:18]

Participants

5

Reactant 3

HCID 123774N,N',N''-TriacetylchitotrioseHCID 1602442-Deoxy-4-O-{2-deoxy-2-[(1-hydroxyethylidene)amino]hexopyranosyl}-2-[(1-hydroxyethylidene)amino]hexoseHCID 439174N-Acetyl-D-Glucosamine

Product 1

HCID 197182N-Acetylchitohexaose

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The combined effluent fractions were freeze-dried to give 36 g of a solid mixture comprising tetra-N-acetylchitotetraose (NACOS-4), penta-N-acetyl-chitopentaose (NACOS-5) and hexa-N-acetyl-chitohexaose (NACOS-6), together with minor proportions of N-acetylglucosamine, di-N-acetyl-chitobiose, tri-N-acetyl-chitotriose. This mixture comprising the water-soluble chitin-oligomers was then chromatographed by a high pressure liquid chromatography on a column of μ-Bondapack CH (a product of Waters Company, U.S.A.) as eluted with methylnitrile-water (70:30 by volume), to effect the isolation of the chitin-oligomers from each other, affording 3.10 g of hexa-N-acetylchitohexaose having an [α]D of -11.2° and a decomposition temperature of 300° C., 7.6 g of penta-N-acetyl-chitopentaose having an [α]D of -9.0° and a decompsition temperature of 304° C.; and 8.1 g of tetra-N-acetyl-chitotetraose having an [α]D of -4.2° and a decomposition temperature of 299° C.

Workup

  1. customwas then chromatographed by a high pressure liquid chromatography on a column of μ-Bondapack CH (a product of Waters Company, U.S.A
  2. wash) as eluted with methylnitrile-water (70:30 by volume)

Sources & evidence

ORD record
ord-937d7eb3d23844798bc07afff31bf720
Source dataset
uspto-grants-1989_02
Patent number
US04804750

Reaction notes

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