Vancomycin → Demannose

HRID 464823Notes

Reaction equation

HRID 464823 reaction equation
C[C@@H]1O[C@@H]([O:8][C@H:9]2[C@H:14]([O:15]C3C4OC5=C(Cl)C=C(C=C5)[C@@H](O)[C@@H]5NC(=O)[C@@H](C6C=CC(O)=C(C7C(O)=CC(O)=CC=7[C@@H](C(O)=O)NC5=O)C=6)NC(=O)[C@H]5C(=CC=3OC3C=CC([C@@H](O)[C@@H](NC([C@H](NC)CC(C)C)=O)C(N[C@@H](CC(N)=O)C(N5)=O)=O)=CC=3Cl)C=4)[O:13][C@H:12]([CH2:95][OH:96])[C@@H:11]([OH:97])[C@@H:10]2[OH:98])C[C@@](N)(C)[C@@H]1O>Cl>[O:15]=[CH:14][C@H:9]([C@H:10]([C@@H:11]([C@@H:12]([CH2:95][OH:96])[OH:13])[OH:97])[OH:98])[OH:8]

Participants

3

Reactant 1

HCID 14969Vancomycin

Product 1

HCID 161658Demannose

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Total hydrolysis of AAD 216A, AAD 216B and AAD 216C, individually, in 6N hydrochloric acid at reflux for 18 hours yielded no common amino acids which could be detected in a standard amino acid analysis. The presence of actinoidinic acid, which is common in the vancomycin class of antibiotics, was confirmed in the hydrolysis products by high pressure liquid chromatography and FAB mass spectrum when compared to an authentic sample. Further, hydrolysis of AAD 216A, AAD 216B and AAD 216C, individually, in 1N hydrochloric acid at reflux for 4 hours yielded mannose but not ristosamine, glucosamine or vancosamine.

Sources & evidence

ORD record
ord-1b0a4b8e7d2c4262826b545aa41cef38
Source dataset
uspto-grants-1985_10
Patent number
US04548974

Reaction notes

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