Amino acid constituents of ristocetin A

Harris, Constance M.; Kibby, Jeffrey J.; Fehlner, James R.; Raabe, Austin B.; Barber, Thomas A.; Harris, Thomas M.

doi:10.1021/ja00496a028

Cited by 35 publications

(11 citation statements)

References 8 publications

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“…Such preconcentration techniques introduce bias and probably restrict the types of siderophores that can be detected. For example, at the natural pH of seawater (∼8), both carboxylate and catecholate type Fe–siderophore complexes will be deprotonated and negatively charged (Harris et al, 1979a; Loomis and Raymond, 1991). Thus, the preconcentration efficiency of catecholate and carboxylate siderophore types onto the commonly used hydrophobic resins (e.g., C18, polystyrene divinyl benzene, XAD) will be reduced.…”

Section: Small Defined Organic Ligandsmentioning

confidence: 99%

“…Thus, the preconcentration efficiency of catecholate and carboxylate siderophore types onto the commonly used hydrophobic resins (e.g., C18, polystyrene divinyl benzene, XAD) will be reduced. Acidification of the sample prior to preconcentration (Mucha et al, 1999; Velasquez et al, 2011), in order to neutralize negatively charged complexed siderophores and thus make them more hydrophobic may also result in siderophore hydrolysis or precipitation (Harris et al, 1979b; Loomis and Raymond, 1991). Changes in sample pH during analysis are also common, with chromatographic separations performed at low pH (McCormack et al, 2003; Velasquez et al, 2011).…”

Section: Small Defined Organic Ligandsmentioning

confidence: 99%

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The organic complexation of iron in the marine environment: a review

Gledhill¹

2012

Front. Microbio.

482

560

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Iron (Fe) is an essential micronutrient for marine organisms, and it is now well established that low Fe availability controls phytoplankton productivity, community structure, and ecosystem functioning in vast regions of the global ocean. The biogeochemical cycle of Fe involves complex interactions between lithogenic inputs (atmospheric, continental, or hydrothermal), dissolution, precipitation, scavenging, biological uptake, remineralization, and sedimentation processes. Each of these aspects of Fe biogeochemical cycling is likely influenced by organic Fe-binding ligands, which complex more than 99% of dissolved Fe. In this review we consider recent advances in our knowledge of Fe complexation in the marine environment and their implications for the biogeochemistry of Fe in the ocean. We also highlight the importance of constraining the dissolved Fe concentration value used in interpreting voltammetric titration data for the determination of Fe speciation. Within the published Fe speciation data, there appear to be important temporal and spatial variations in Fe-binding ligand concentrations and their conditional stability constants in the marine environment. Excess ligand concentrations, particularly in the truly soluble size fraction, seem to be consistently higher in the upper water column, and especially in Fe-limited, but productive, waters. Evidence is accumulating for an association of Fe with both small, well-defined ligands, such as siderophores, as well as with larger, macromolecular complexes like humic substances, exopolymeric substances, and transparent exopolymers. The diverse size spectrum and chemical nature of Fe ligand complexes corresponds to a change in kinetic inertness which will have a consequent impact on biological availability. However, much work is still to be done in coupling voltammetry, mass spectrometry techniques, and process studies to better characterize the nature and cycling of Fe-binding ligands in the marine environment.

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Section: Small Defined Organic Ligandsmentioning

confidence: 99%

Section: Small Defined Organic Ligandsmentioning

confidence: 99%

The organic complexation of iron in the marine environment: a review

Gledhill¹

2012

Front. Microbio.

482

560

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“…It is therefore anticipated that a similar partial removal of the glycoside moiety from the actaplanins would also occur here resulting in the formation of X and Y. This observation and the fact that all actaplanins gave rise to the same '-aglycone (1) confirms that all actaplanins have the same peptide core but different neutral sugar side chains. Total acid hydrolysis of the products also gave the identical amino acids by the amino acid analyses.…”

Section: Resultsmentioning

confidence: 52%

“…Several recent structural studies of glycopeptide antibiotics1~5) have shown that these antibiotics appear to hold several chemical features in common. Typically, glycopeptides give rise to an "aglycone," neutral sugars"') and an amino sugar upon mild hydrolysis', [1][2][3][4][5][6][7][8][9][10][11][12]. Furthermore, the aglycone is a complex peptide which retains the same amino acids present in the parent after total hydrolysis and also some of the antimicrobial activity of the parent.…”

Section: Bacteriamentioning

confidence: 99%

Actaplanin, new glycopeptide antibiotics produced by Actinoplanes missouriensis. The isolation and preliminary chemical characterization of actaplanin.

Debono¹,

Merkel

Molloy

et al. 1984

J. Antibiot.

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Actaplanin (A4696), a new complex of broad spectrum Gram-positive antibiotics is produced by Actinoplanes inissouriensis. High performance liquid chromatography was used to show that this complex is composed of several actaplanins.Hydrolytic experiments with actaplanins A, B,, B., B3, C, and G showed that these actaplanins were composed of the same peptide core, an amino sugar and varying amounts of glucose, mannose and rhamnose. The neutral sugar content was determined for each actaplanin. A bioautographic study of aglycone formation during hydrolysis of the actaplanin complex showed that within a short time a simple mixture of two antimicrobially active hydrolysis products was obtained. These substances retained the antimicrobial spectrum and a high percentage of the antibiotic activity of the parent actaplanin complex.Methanolysis of the actaplanin complex as well as the individual actaplanins resulted in the selective loss of the neutral sugar moieties and the isolation of actaplanin T(pseudo)-aglyconethe core peptide which still retained an amino sugar group. The 1H NMR spectrum of this substance indicated a similarity to many features of ristocetin ?Ir aglycone. Hydrolytic studies showed that the amino sugar present in actaplanin was identical with L-ristosamine. It is concluded that the aglycone of actaplanin is a complex peptide composed of aromatic amino acids, and that the actaplanins each possess this aglycone and L-ristosamine but are differentiated by their neutral sugar composition. Actaplanin (A4696)**, a new complex of glycopeptide antibiotics produced by Actinoplanes missouriensis (ATCC 23342), exhibits strong inhibitory activity against a broad spectrum of Gram-positive bacteria.The isolation of the actaplanin complex showed that actaplanin was composed of several closely related glycopeptide components (hereafter referred to as actaplanins) by their chromatographic behavior.Several recent structural studies of glycopeptide antibiotics1~5) have shown that these antibiotics appear to hold several chemical features in common. Typically, glycopeptides give rise to an "aglycone," neutral sugars"') and an amino sugar upon mild hydrolysis',1-12). Furthermore, the aglycone is a complex peptide which retains the same amino acids present in the parent after total hydrolysis and also some of the antimicrobial activity of the parent.The purpose of the present study was to determine the general chemical characteristics of the actaplanin complex and to relate the differences and the similarities it bears to known members of its class". The chemical relationship between the various actaplanins has also been determined.

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“…Euphorbia helioscopa [143] Enduracidin A and B; vancomycin [285,286]; ristocetin [287]; ristomycin [411]; actintoidin [408]; avoparcin A355l2B (antibiotic); Caesalpinia tinctoria [284]; Iris sanguinea [5] (tryptophan metabolism) see Table 4.1 for this and other kynurenine derivatives Streptomyces mitakaensis [6]; Fagus phloem sap [10] Canthium euryoides [298] Ristomycin [303,304] Microspira tyrosinatica [296] Cycloheptamycin [145] Puromycin [I, 3] In human urine [429] Stravidin [305] (Streptomyces avidini/) Mytilus gal/oprovincialis [51] Mytilus gal/oprovincialis [51] Palythoa tuberculosa [153] Palythoa tuberculosa [154] (Zoantharia); Chondrus yendoi [152] (red alga)…”

Section: -Hydroxyphenylglycinementioning

confidence: 99%

The Non-Protein Amino Acids

Hunt¹

1985

Chemistry and Biochemistry of the Amino Acids

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Amino acid constituents of ristocetin A

Cited by 35 publications

References 8 publications

The organic complexation of iron in the marine environment: a review

The organic complexation of iron in the marine environment: a review

Actaplanin, new glycopeptide antibiotics produced by Actinoplanes missouriensis. The isolation and preliminary chemical characterization of actaplanin.

The Non-Protein Amino Acids

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