1999
DOI: 10.7164/antibiotics.52.710
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Rhodopeptins, Novel Cyclic Tetrapeptides with Antifungal Activities from Rhodococcus sp. III. Synthetic Study of Rhodopeptins.

Abstract: Total syntheses of cyclo (-Gly-L-Lys-L-Val-(i?)-3-aminododecanoyl-); LV9nA and its diastereomer cyclo (-Gly-L-Lys-L-Val-(S)-3-aminododecanoyl-); LV9nB, congeners of rhodopeptin B5 on /3-amino acid moiety, were achieved. The /3-amino acid moiety was prepared as a racemate by the thermal Michael addition of an amine to a,/3-unsaturated ester. The racemic fiamino acids were converted to their L-Valylamide derivatives and the obtained diastereomers were separated.

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Cited by 20 publications
(22 citation statements)
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“…RJB may be involved in control of the expression of one or more of these clusters. Although a few Rhodococcus antimicrobials are known 41 – 44 this genus has remained largely unexplored for production of secondary metabolites. In this work, we detected bioactivity of R .…”
Section: Discussionmentioning
confidence: 99%
“…RJB may be involved in control of the expression of one or more of these clusters. Although a few Rhodococcus antimicrobials are known 41 – 44 this genus has remained largely unexplored for production of secondary metabolites. In this work, we detected bioactivity of R .…”
Section: Discussionmentioning
confidence: 99%
“…Additionally, multiple Rhodococcus strains have also been reported to produce antibiotics [ 21 ]. Four (groups of) rhododoccal natural products with antimicrobial activity have been described in literature; lariantin peptide antibiotics with anti-mycobacterial activity [ 22 ], the polyketide aurachin RE from Rhodococcus erythropolis JCM 6824 (which has a structure similar to that of aurachin C from the Gram-negative organism Stigmatella aurantiaca [ 23 , 24 ]), a group of peptide antifungals named rhodopeptins [ 25 ] and the recently described humimycins [ 26 ]. The gene cluster responsible for the synthesis of rhodopeptins has not yet been identified.…”
Section: Introductionmentioning
confidence: 99%
“…Members of the genus Rhodococcus have been reported to show antifungal activity in vitro against plant-pathogenic fungi ( Chiba et al, 1999 ; Iwatsuki et al, 2007 ; Santos et al, 2020 ) and RL1 reduced growth of F. oxysporum in vitro , but showed no inhibition against R. solani and F. culmorum ( Supplementary Figure 4 ). Further studies using model plants will reveal the full potential of RL1 as biocontrol agent against plant pathogenic fungi.…”
Section: Discussionmentioning
confidence: 99%