133705-25-6

Usage

InChI:InChI=1/C38H48N4O13/c1-36(33(47)48,21-9-11-23-41(54)31(45)19-17-27-13-5-3-6-14-27)39-29(43)25-38(53,35(51)52)26-30(44)40-37(2,34(49)50)22-10-12-24-42(55)32(46)20-18-28-15-7-4-8-16-28/h3-8,13-20,53-55H,9-12,21-26H2,1-2H3,(H,39,43)(H,40,44)(H,47,48)(H,49,50)(H,51,52)/b19-17+,20-18+/t36-,37-/m0/s1

Upstream product

• 114340-52-2 3-(tert-butoxycarbonyl)-3-hydroxypentanedioic acid 
• 114340-53-3 2-tert-butyl-1,3-di-N-(hydroxyl) succinimidyl citrate 
• 145385-51-9 N^ε-cinnamoyl-N^ε-hydroxy-N^α-BOC-L-lysine methyl ester 
• 145385-50-8 N^α,N^α'-<3-hydroxy-3-tert-(tert-butoxycarbonyl)glutaryl>bisε-cinnamoyl-N^ε-(benzoyloxy)-L-lysine methyl ester> 
• 145385-46-2 N^ε-cinnamoyl-N^ε-(benzoyloxy)-N^α-BOC-L-lysine methyl ester 
• 55757-60-3 N-α-(tert-butoxycarbonyl)-L-lysine methyl ester 
• 152922-81-1 (E)-3-phenyl-N-phenylmethoxy-2-propenamide 
• 81505-59-1 (L)-N-Boc-ε-hydroxynorleucine methyl ester 
• 140-10-3 (E)-3-phenylacrylic acid 
• 183890-46-2 (S)-2-(3-tert-Butoxycarbonyl-3-hydroxy-4-{(S)-1-methoxycarbonyl-5-[[(E)-(3-phenyl-acryloyl)]-(2-trimethylsilanyl-ethoxy)-amino]-pentylcarbamoyl}-butyrylamino)-6-[[(E)-(3-phenyl-acryloyl)]-(2-trimethylsilanyl-ethoxy)-amino]-hexanoic acid methyl ester 
• 158414-69-8 (-)-(S)-6-oxo-2-piperidinecarboxylic acid methyl ester 
• 1025782-34-6 6-hydroxypiperidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester 
• 97347-42-7 (+)-(S)-N₂,N₆-bis[(1,1-dimethylethoxy)carbonyl]-6-oxo-lysine methyl ester 
• 183890-47-3 (S)-2-(3-Carboxy-3-hydroxy-4-{(S)-1-methoxycarbonyl-5-[[(E)-(3-phenyl-acryloyl)]-(2-trimethylsilanyl-ethoxy)-amino]-pentylcarbamoyl}-butyrylamino)-6-[[(E)-(3-phenyl-acryloyl)]-(2-trimethylsilanyl-ethoxy)-amino]-hexanoic acid methyl ester 

Relevant academic research and scientific papers

A total synthesis of nannochelin A. A short route to optically active Nω-hydroxy-α-amino acid derivatives

The total synthesis of nannochelin A, a lysine-basd cinnamoyl hydroxamate produced by Nannocystis exedens, is described. The key transformation involves construction of the Nε-cinnamoyl-Nε-hydroxy-L-lysine methyl ester fragment by partial reduction of the lactam carbonyl of 6 derived from L-lysine, oximation of this aldehyde equivalent compound 8 with O-[2-(trimethylsilyl)ethyl]hydroxylamine, and reduction of the oxime 10, followed by N-acylation prior to coupling with the external carbonyls of citric acid. This methodology will be applicable to synthesis of other hydroxamate-containing siderophores bearing hydrogenolyzable groups in the molecule.

Synthesis of the hydroxamate siderophore nannochelin A

A total synthesis of nannochelin A, a novel cinnamoyl-hydroxamate siderophore produced by Nannocystis exedens, is described.