Vancomycin → Demannose

HRID 2291645Notes

Reaction equation

HRID 2291645 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 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 IN hydrochloric acid at reflux for 4 hours yielded mannose but not ristosamine, glucosamine or vancosamine.

Sources & evidence

ORD record
ord-180f70b924de46b5af3ddedf5554ce5e
Source dataset
uspto-grants-1989_01
Patent number
US04797280

Reaction notes

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