Structure elucidation of the teicoplanin antibiotics

Barna, Jennifer C. J.; Williams, Dudley H.; Stone, David J.; Leung, T. W.; Doddrell, David M.

doi:10.1021/ja00329a044

Cited by 135 publications

(72 citation statements)

References 6 publications

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“…These data suggest that removal of chlorine in the aromatic ring of amino acid 6 has slight, if any, effect on antibacterial activity. However, removal of chlorine in the aromatic ring of amino acid 2 diminishes the activity 10-fold. Finally, the selective and sequential removal of first the L-epivancosamine and then the second glucose from amino acid 4 of A82846 was accomplished. These two compounds and A82846B are 2 to 10 times more active than vancomycin.…”

Section: Structure-activity Relationships (Sar)mentioning

confidence: 99%

Antibacterial activities and modes of action of vancomycin and related glycopeptides

Ramakrishnan

1991

Antimicrob Agents Chemother

130

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Section: Structure-activity Relationships (Sar)mentioning

confidence: 99%

Antibacterial activities and modes of action of vancomycin and related glycopeptides

Ramakrishnan

1991

Antimicrob Agents Chemother

130

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“…Teichomycin A-2 components differ in the structure of a fatty acid moiety linked by an amide bond to a glucosamine residue (Barna et al, 1984). As shown in Abbreviation: FAME, fatty acid methyl ester.…”

Section: Introductionmentioning

confidence: 99%

Factors affecting the normal and branched-chain acyl moieties of teicoplanin components produced by Actinoplanes teichomyceticus

Borghi¹,

Edwards²,

Zerilli³

et al. 1991

Journal of General Microbiology

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Teicoplanin, a glycopeptide antibiotic produced by Actinopfanes teichornyceticus, comprises five main components, denoted T-A2-1 to T-A2-5, differing in the structure of their acyl side chain, which is linear in T-A2-1 and T-A2-3 and branched in the other components. Production of T-A2-1, characterized by a linear C1O:l acyl moiety, is entirely dependent on the presence of linoleate in the fermentation medium. Addition to the medium of oleic acid esters at 2 g 1-l increases the yields of T-A2-3, characterized by a linear C1O:O acyl chain, about threefold. The antibiotic linear side chains thus appear to originate from C18 unsaturated acid by P-oxidation degradation. The percentage of T-A2-2, T-A2-4 and T-A2-5, bearing the iso-ClO:O, anteiso-Cll :O and iso-Cl1 :O acyl moieties, respectively, is strongly influenced by the presence in the medium of the amino acids known to be precursors of branched-chain fatty acids. Thus, valine increases the production of T-A2-2 whereas isoleucine or leucine increase the relative yields of T-A2-4 or T-A2-5, respectively. Analysis of the total cell lipids upon addition of the same amino acid shows corresponding increases in the proportion of the iso-Cl6 : 0, iso-Cl5 : 0 or anteiso-C17 : 0. A mutant A. teichornyceticus strain, which produces a novel teicoplanin with a linear 0 : 0 chain, differs from the wild strain in the presence of the linear C17: 1 acid in its lipids. The relative incorporation of [14C]acetate into teicoplanin acyl moieties is substantially lower when this precursor is added to grown A. teichornyceticus mycelium rather than at the time of inoculation. The results suggest that teicoplanin branched acyl moieties also originate from P-oxidation degradation of cellular long-chain fatty acids.

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“…This is produced by Actinoplanes teichomyceticus and is active against aerobic and anaerobic Gram-positive bacteria both in vitro and in vivo [18,35]. The aglycone consists of four fused macrocyclic rings which form a "semirigid basket" (Fig.…”

Section: Teicoplaninmentioning

confidence: 99%

“…It contains seven aromatic rings, two of which have chlorine-substituents and four of which are ionizable phenolic moieties. The aglycone contains a single primary amine which (together with the phenolic moieties) maintains its charge at the pHs normally used in HPLC (i. e. pH 3. nin is a mixture of five closely related analogs, designated T-A 2-1 through T-A 2-5 [35,36]. They differ by approximately 20 molecular mass units because of the variation in length (i. e. C 10 -C 11 ) and substituent groups of the acyl side-chain attached to the amino sugar.…”

Section: Teicoplaninmentioning

confidence: 99%

HPLC separation of amino acid enantiomers and small peptides on macrocyclic antibiotic‐based chiral stationary phases: A review

Ilisz

Berkecz

Péter

2006

J of Separation Science

159

105

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The search for new and effective chiral selectors capable of separating a wide variety of enantiomeric compounds is an ongoing process. In the past decade, macrocyclic antibiotics have proved to be an exceptionally useful class of chiral selectors for the separation of enantiomers of biological and pharmacological importance by means of HPLC, TLC and electrophoresis. More chiral analytes have been resolved through the use of glycopeptides than with all the other macrocyclic antibiotics combined (ansamycins, thiostrepton, aminoglycosides, etc.). The glycopeptides avoparcin, teicoplanin, ristocetin A and vancomycin have been extensively used as chiral selectors in the form of chiral bonded phases in HPLC, and HPLC stationary phases based on these glycopeptides have been commercialized. Teicoplanin, vancomycin, their analogs and ristocetin A seem to be the most useful glycopeptide HPLC bonded phases for the enantioseparation of proteins and unusal native and derivatized amino acids. In fact, the macrocyclic glycopeptides are to some extent complementary to one another: where partial enantioresolution is obtained with one glycopeptide, there is a high probability that baseline or better separation can be obtained with another. This review sets out to characterize the physicochemical properties of these antibiotics and their application in the enantioseparations of amino acids. The mechanism of separation, the sequence of elution of the stereoisomers and the relation to the absolute configuration are also discussed.

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Structure elucidation of the teicoplanin antibiotics

Cited by 135 publications

References 6 publications

Antibacterial activities and modes of action of vancomycin and related glycopeptides

Antibacterial activities and modes of action of vancomycin and related glycopeptides

Factors affecting the normal and branched-chain acyl moieties of teicoplanin components produced by Actinoplanes teichomyceticus

HPLC separation of amino acid enantiomers and small peptides on macrocyclic antibiotic‐based chiral stationary phases: A review

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