55598-85-1

Usage

InChI:InChI=1/C66H74Cl2N8O25/c1-23(2)12-34(70-5)58(87)75-49-51(82)26-7-10-38(32(67)14-26)97-40-16-28-17-41(55(40)101-65-56(54(85)53(84)42(22-77)99-65)100-44-21-66(4,69)57(86)24(3)96-44)98-39-11-8-27(15-33(39)68)52(83)50-62(91)74-48(64(94)95)31-18-29(78)19-37(80)45(31)30-13-25(6-9-36(30)79)46(59(88)76-50)73-60(89)47(28)72-43(81)20-35(63(92)93)71-61(49)90/h6-11,13-19,23-24,34-35,42,44,46-54,56-57,65,70,77-80,82-86H,12,20-22,69H2,1-5H3,(H,71,90)(H,72,81)(H,73,89)(H,74,91)(H,75,87)(H,76,88)(H,92,93)(H,94,95)

Upstream product

• 1404-90-6 vancomycin 

Relevant academic research and scientific papers

STABILIZED VANCOMYCIN FORMULATIONS

In one aspect, the invention provides a stabilized lipid-based glycopeptide antibiotic composition and a process for producing the same. In another aspect, the invention provides methods for treating a bacterial pulmonary infection by administering to a subject in need thereof a therapeutically effective amount of the stabilized lipid-based glycopeptide antibiotic composition.

Vancomycin: Structure and Transformation to CDP-I

The structure of vancomycin is assigned as 7 in which aspartate is present as asparagine, rather than isoasparagine (i.e., 4) as had been proposed previously (Williamson, M.P.; Williams, D.H.J.Am.Chem.Soc. 1981, 103, 6580).The mechanism of rearrangement of vancomycin to CDP-I has been investigated.The pathway is deduced: vancomycin -> succinimide 11 -> CDP-I-m (3) CDP-I-M (2).Succinimide 11 has been isolated and characterized by FT-IR and FAB-MS; these data are in agreement with an in-chain succinimide but not a seco structure.Treatment of 11 at pH 8 leads to immediate appearance of the minor form of CDP-I, which slowly yields an equilibrium mixture with the major form (ca. 64:36 of 2:3).No major change in the equilibrium ratio or rate of equilibration was found by changing solvent (H2O, Me2SO, or 0.1percent TFA/20percent 2-propanol) or pH (in the range 2.0-8.0).High-field 1H NMR studies of 2 and 3 indicate that they are atropisomers involving different orientations of the Cl-substituted aromatic ring of residue 2, in agreement with earlier assignments by Williamson and Williams.It is concluded that 2 and 3 can interconvert by simple reorientation of the aromatic ring rather than via a transient cleavage product.The cyclophane ring in which the Cl-substituted aromatic residue 2 is embedded is enlarged by one methylene unit in the conversion of vancomycin to CDP-I; rotation of ring 2 can occur in CDP-I but not in vancomycin.The additional methylene unit in the N-terminal cyclophane ring of CDP-I causes the ring to lie in a conformation that is significantly different from that of vancomycin.