112972-60-8

Usage

InChI:InChI=1/C18H32N4O6/c23-15-7-10-18(26)22(28)14-6-2-4-12-20-16(24)8-9-17(25)21(27)13-5-1-3-11-19-15/h27-28H,1-14H2,(H,19,23)(H,20,24)

Upstream product

• 111-24-0 1,5-dibromo-pentane 
• 203189-78-0 N-hydroxy-N-succinyl-putrescine 
• 129245-24-5 5,16-bis(benzyloxy)-20-cyano-4,12,15-trioxo-5,11,16-triazaeicosanoic acid 
• 129245-21-2 O-benzyl-N-(5-aminopentyl)-N-(tert-butoxycarbonyl)hydroxylamine 
• 6280-87-1 δ-chlorovaleronitrile 
• 129245-26-7 6,17-bis(benzyloxy)-1,6,12,17-tetraazacyclodocosane-2,5,13,16-tetrone 
• 129245-25-6 21-amino-5,16-bis(benzyloxy)-4,12,15-trioxo-5,11,16-triazaheneicosanoic acid 
• 128173-50-2 O-Benzyl-N-(tert-butoxycarbonyl)-N-(4-cyanobutyl)-hydroxylamine 
• 112139-59-0 O-benzyl-N-(4-cyanobutyl)-hydroxylamine 
• 129245-22-3 N-(4-cyanobutyl)-3-<<5-<(benzyloxy)-tert-butoxy-carbonylamino>pentyl>carbamoyl>-O-benzylpropionohydroxamic acid 
• 129245-23-4 N-(4-cyanobutyl)-3-<<5-<(benzyloxy)amino>pentyl>carbamoyl>-O-benzylpropionohydroxamic acid 
• 112139-60-3 N-(4-Cyanobutyl)-N-(benzyloxy)succinamic Acid 

Related news

Simultaneous biosynthesis of putrebactin, avaroferrin and BISUCABERIN (cas 112972-60-8) by Shewanella putrefaciens and characterisation of complexes with iron(III), molybdenum(VI) or chromium(V)07/27/2019

Cultures of Shewanella putrefaciens grown in medium containing 10 mM 1,4-diamino-2-butanone (DBO) as an inhibitor of ornithine decarboxylase and 10 mM 1,5-diaminopentane (cadaverine) showed the simultaneous biosynthesis of the macrocyclic dihydroxamic acids: putrebactin (pbH2), avaroferrin (avH2...detailed

Relevant academic research and scientific papers

One Enzyme to Build Them All: Ring-Size Engineered Siderophores Inhibit the Swarming Motility of Vibrio

Bacteria compete for ferric iron by producing siderophores, and some microbes engage in piracy by scavenging siderophores of their competitors. The macrocyclic hydroxamate siderophore avaroferrin of Shewanella algae inhibits swarming of Vibrio alginolyticus by evading this piracy. Avaroferrin, as well as related putrebactin and bisucaberin, are produced by the IucC-like synthetases AvbD, PubC, and BibCC. Here, we have established that they are capable of synthesizing not only their native product but also other siderophores. Exploiting this relaxed substrate specificity by synthetic precursors generated 15 different ring-size engineered macrocycles ranging from 18- to 28-membered rings, indicating unprecedented biosynthetic flexibility of the enzymes. Two of the novel siderophores could be obtained in larger quantities by precursor-directed biosynthesis in S. algae. Both inhibited swarming motility of Vibrio and, similar to avaroferrin, the most active one exhibited a heterodimeric architecture. Our results demonstrate the impact of minor structural changes on biological activity, which may trigger the evolution of siderophore diversity.

Convergent Synthesis of Macrocyclic and Linear Desferrioxamines

Polyhydroxamate desferrioxamines (DFO) are nontoxic siderophores endowed with high potential for development of therapeutic chelating agents. Herein, we report a modular and convergent strategy for diverse synthesis of macrocyclic and linear DFOs. The strategy employed orthogonally protected N-hydroxy-N-succinylcadaverine building blocks, which allowed bidirectional extension of the DFO structure. The efficiency of the new strategy was demonstrated by the total synthesis of 44-membered macrocyclic DFO-T1, as well as four related DFO compounds in 11–13 linear steps and 2.1 %–10 % overall yields. Comparison of the iron binding affinity of the DFOs revealed DFO-E as the best chelator.

Bisucaberin biosynthesis: An adenylating domain of the BibC multi-enzyme catalyzes cyclodimerization of N-hydroxy-N-succinylcadaverine

The bisucaberin biosynthetic gene cluster has been identified in Vibrio salmonicida and a domain from within the BibC multienzyme encoded by the cluster has been shown to catalyse ATP-dependent dimerisation and macrocyclisation of N-hydroxy-N-succinylcadaverine to form bisucaberin. The Royal Society of Chemistry.

THE TOTAL SYNTHESIS OF BISUCABERIN

The first total synthesis of 6,17-dihydroxy-1,6,12,17-tetraazacyclodocosane-2,5,13,16-tetrone (bisucaberin) is presented.The synthetic scheme employed in this study illustrates the utility of O-benzyl-N-(tert-butoxycarbonyl)-N-(4-cyanobutyl)hydroxylamine