A New and Improved Method for Deglycosidation of Glycopeptide Antibiotics Exemplified with Vancomycin, Ristocetin, and Ramoplanin.

Wanner, Jutta; Tang, Datong; McComas, Casey C.; Crowley, Brendan M.; Jiang, Wanlong; Moss, Jason A.; Boger, Dale L.

doi:10.1002/chin.200328229

Cited by 6 publications

(15 citation statements)

References 1 publication

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“…We observed that deglycosidation of the monoglycosidetype vancomycin (2) and of the bis-glycoside-type eremomycin (1) with HF/anisole under the conditions suggested by the American researchers [5] (Scheme 1) furnished the homogeneous aglyco-vancomycin (4) and aglyco-eremomycin (3) with good yields. The purity of the products was proved by TLC, HPLC, and MALDI-TOF (Table 1), and the structures were assigned according to the 1 H and 13 C NMR data (Table 2aϳb).…”

Section: Deglycosidationmentioning

confidence: 85%

“…This aglycone (6) was found twice as active against MRSA as the parent antibiotic (5). As compared to 5, the activity of 6 against both Enterococcus faecalis strains dropped to half, and to one-fourth against B. subtilis.…”

Section: Antibacterial Activitymentioning

confidence: 97%

“…However, these procedures generally led to extremely complex reaction mixtures and low yields. The hydrogen fluoride-method was used by Wanner [5] in glycopeptide chemistry for the deglycosidation of vancomycin, ristocetin and ramoplanin.…”

Section: A New Series Of Glycopeptide Antibiotics Incorporating a Squmentioning

confidence: 99%

“…Deglycosidation of eremomycin and vancomycin was carried out as described earlier by Wanner et al [5] (25°C, 2 hours). The physico-chemical data of the prepared aglycones 3 and 4 are collected in Table 1, and the NMR data are presented in Tables 2aϳb.…”

Section: Deglycosidation Of Eremomycin and Vancomycinmentioning

confidence: 99%

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A New Series of Glycopeptide Antibiotics Incorporating a Squaric Acid Moiety

et al. 2006

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The aglycones of the antibiotics eremomycin, vancomycin and ristocetin (3, 4 and 6, respectively) were prepared by deglycosidation of the parent antibiotics with hydrogen fluoride, and complete assignation of their 1 H, 13 C and 15 N spectra was performed. The squaric acid amide esters (11ϳ14), were prepared from dimethyl squarate. The corresponding asymmetric diamides (16ϳ19, 22, 23) were also synthesized using 4-phenylbenzylamine and triglycine. The advantage of the method is the high regioselectivity and that no protecting group strategy is required. Electrospray mass spectroscopic method was elaborated for the determination of the site of substitution of the modified antibiotics. The antibacterial activity of the prepared compounds is discussed in detail.

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Section: Deglycosidationmentioning

confidence: 85%

Section: Antibacterial Activitymentioning

confidence: 97%

Section: A New Series Of Glycopeptide Antibiotics Incorporating a Squmentioning

confidence: 99%

Section: Deglycosidation Of Eremomycin and Vancomycinmentioning

confidence: 99%

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A New Series of Glycopeptide Antibiotics Incorporating a Squaric Acid Moiety

et al. 2006

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“…Our studies have shown that aglyco-ristocetin (2), prepared (Scheme 1) by means of deglycosylation [12] of 1, retains the antibacterial activity (Table 1) and this effect is comparable [13] to that of vancomycin, teicoplanin and linezolid used in clinical practice. However, 2 is not suitable for thrombocyte-aggregation tests due to its extremely limited solubility in water.…”

Section: Resultsmentioning

confidence: 71%

N-Glycosylthioureido Aglyco-ristocetins without Platelet Aggregation Activity

et al. 2007

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The water-soluble N-methoxy-PEG-yl-, N-b-Dglucopyranosyl-and N-b -D-maltosylthioureido aglycoristocetin were prepared which, in contrast to ristocetin A, did not induce thrombocyte aggregation. The antibacterial activity of N-b -D-maltosylthioureido aglyco-ristocetin A against MRSA was comparable to that of ristocetin A, while its activity against Enterococcus faecalis (VRE, TSE) is somewhat stronger when compared to those of vancomycin and ristocetin A.

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