
Angewandte Chemie - International Edition p. 4342 - 4346 (2017)
Update date:2022-08-05
Topics:
Montes Vidal, Diogo
von Rymon-Lipinski, Anna-Lena
Ravella, Srinivasa
Groenhagen, Ulrike
Herrmann, Jennifer
Zaburannyi, Nestor
Zarbin, Paulo H. G.
Varadarajan, Adithi R.
Ahrens, Christian H.
Weisskopf, Laure
Müller, Rolf
Schulz, Stefan
The analysis of volatiles from bacterial cultures revealed long-chain aliphatic nitriles, a new class of natural products. Such nitriles are produced by both Gram-positive Micromonospora echinospora and Gram-negative Pseudomonas veronii bacteria, although the structures differ. A variable sequence of chain elongation and dehydration in the fatty acid biosynthesis leads to either unbranched saturated or unsaturated nitriles with an ω?7 double bond, such as (Z)-11-octadecenenitrile, or methyl-branched unsaturated nitriles with the double bond located at C-3, such as (Z)-13-methyltetradec-3-enenitrile. The nitrile biosynthesis starts from fatty acids, which are converted into their amides and finally dehydrated. The structures and biosyntheses of the 19 naturally occurring compounds were elucidated by mass spectrometry, synthesis, and feeding experiments with deuterium-labeled precursors. Some of the nitriles showed antimicrobial activity, for example, against multiresistant Staphylococcus aureus strains.
View MoreChangzhou Ansciep Chemical Co.,Ltd.
Contact:+86 519 8630 5871
Address:A-710 Boan International, 8 East Guangdian Road,Wujin,Changzhou
Jinan Kaypharm Chemical Co.,Ltd
Contact:86-0531-86986780
Address:Room101,No189-2,Huayuan Road,Jinan City,Shandong Province
Jinan Jinguilin Chemical Co.,Ltd
Contact:+86-531-81188412
Address:3rd floor of Torch Building, Huanyuan Rd, City of Jinan
Contact:0572-2722882
Address:1201,F3,xinghuibandao,
Zhejiang Chemicals Import & Export Corporation (ZHECHEM)
Contact:+86-571-87046953
Address:No. 37, Qingchun Road
Doi:10.1016/j.ica.2006.02.030
(2006)Doi:10.1039/c39830001147
(1983)Doi:10.1021/jo00183a024
(1984)Doi:10.1021/ol7022856
(2007)Doi:10.1002/cctc.202100051
(2021)Doi:10.1021/jm401610c
(2013)