HCID 178430952, compound → Demannose

HRID 2072383Notes

Reaction equation

HRID 2072383 reaction equation
[CH3:1][C:2]1[C:7]([NH2:8])=[N:6][C:5]([C@@H:9]([NH:14][CH2:15][C@H:16]([NH2:20])[C:17]([NH2:19])=[O:18])[CH2:10][C:11]([NH2:13])=[O:12])=[N:4][C:3]=1[C:21]([NH:23][C@H:24]([C:57]([NH:59][C@@H:60]([C@@H:62]([OH:96])[C@@H:63]([C:65]([NH:67][C@H:68]([C:72]([NH:74][CH2:75][CH2:76][C:77]1[S:81][CH:80]=[C:79]([C:82]2[S:86][C:85]([C:87]([NH:89][CH2:90][CH2:91][CH2:92][S+:93]([CH3:95])[CH3:94])=[O:88])=[CH:84][N:83]=2)[N:78]=1)=[O:73])[C@H:69]([OH:71])[CH3:70])=[O:66])[CH3:64])[CH3:61])=[O:58])[C@@H:25]([O:31][C@@H:32]1[O:37][C@@H:36]([CH2:38][OH:39])[C@@H:35]([OH:40])[C@H:34]([OH:41])[C@@H:33]1[O:42][C@H:43]1[O:48][C@H:47]([CH2:49][OH:50])[C@@H:46]([OH:51])[C@H:45]([O:52][C:53]([NH2:55])=[O:54])[C@@H:44]1[OH:56])[C:26]1[N:30]=[CH:29][NH:28][CH:27]=1)=[O:22]>CO>[CH3:1][C:2]1[C:7]([NH2:8])=[N:6][C:5]([C@@H:9]([NH:14][CH2:15][C@H:16]([NH2:20])[C:17]([NH2:19])=[O:18])[CH2:10][C:11]([NH2:13])=[O:12])=[N:4][C:3]=1[C:21]([NH:23][C@H:24]([C:57]([NH:59][C@@H:60]([C@@H:62]([OH:96])[C@@H:63]([C:65]([NH:67][C@H:68]([C:72]([NH:74][CH2:75][CH2:76][C:77]1[S:81][CH:80]=[C:79]([C:82]2[S:86][C:85]([C:87]([NH:89][CH2:90][CH2:91][CH2:92][S+:93]([CH3:94])[CH3:95])=[O:88])=[CH:84][N:83]=2)[N:78]=1)=[O:73])[C@H:69]([OH:71])[CH3:70])=[O:66])[CH3:64])[CH3:61])=[O:58])[C@@H:25]([O:31][C@@H:32]1[O:37][C@@H:36]([CH2:38][OH:39])[C@@H:35]([OH:40])[C@H:34]([OH:41])[C@@H:33]1[O:42][C@H:43]1[O:48][C@H:47]([CH2:49][OH:50])[C@@H:46]([OH:51])[C@H:45]([O:52][C:53]([NH2:55])=[O:54])[C@@H:44]1[OH:56])[C:26]1[N:30]=[CH:29][NH:28][CH:27]=1)=[O:22].[O:31]=[CH:32][C@@H:33]([C@@H:34]([C@H:35]([C@@H:36]([CH2:38][OH:39])[OH:37])[OH:40])[OH:41])[OH:42].[O:31]=[CH:32][C@H:33]([C@H:34]([C@@H:35]([C@@H:36]([CH2:38][OH:39])[OH:37])[OH:40])[OH:41])[OH:42]

Participants

5

Reactant 1

HCID 178430952HCID 178430952, compound

Product 3

HCID 161658DemannoseHCID 167792guloseHCID 178430952HCID 178430952, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The sugar component of Bu-2231 A and B was. also investigated comparatively with bleomycin. A mixture of components A and B was refluxed in methanol with a strongly acidic resin (Amberlyst 15) for 20 hours. Basic fragments from the hydrolysis were adsorbed on the resin and neutral products liberated in the solution were concentrated in vacuo to a sticky syrup. This material was trimethylsilyated and then subjected to gas-chromatographic analysis. Bleomycin gave peaks assignable to gulose and mannose, and the Bu-2231 components showed nearly the same elution pattern as that of bleomycin, indicating the same structure of the carbohydrate portion in the antibiotics.

Workup

  1. additionA mixture of components A and B
  2. concentrationwere concentrated in vacuo to a sticky syrup

Sources & evidence

ORD record
ord-e3597d2d85524faa89c001f1b75fc04c
Source dataset
uspto-grants-1977_09
Patent number
US04051237

Reaction notes

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