6061-13-8Relevant articles and documents
Structures and Biosynthetic Pathway of Coprisamides C and D, 2-Alkenylcinnamic Acid-Containing Peptides from the Gut Bacterium of the Carrion Beetle Silpha perforata
Shin, Yern-Hyerk,Ban, Yeon Hee,Kim, Tae Ho,Bae, Eun Seo,Shin, Jongheon,Lee, Sang Kook,Jang, Jichan,Yoon, Yeo Joon,Oh, Dong-Chan
, (2021/02/26)
Coprisamides C and D (1 and 2) were isolated from a gut bacterium, Micromonospora sp. UTJ3, of the carrion beetle Silpha perforata. Based on the combined analysis of UV, MS, and NMR spectral data, the planar structures of 1 and 2 were elucidated to be unreported derivatives of coprisamides A and B, cyclic depsipeptides bearing a 2-alkenylcinnamic acid unit and the unusual amino acids β-methylaspartic acid and 2,3-diaminopropanoic acid. The absolute configuration of 1 was determined using the advanced Marfey's method, phenylglycine methyl ester derivatization, and J-based configuration analysis. The biosynthetic gene clusters for the coprisamides were investigated based on genomic data from coprisamide-producing strains Micromonospora sp. UTJ3 and Streptomyces sp. SNU533. Coprisamide C (1) was active against the Mycobacterium tuberculosis mc26230 strain.
Organocatalytic synthesis of β-alkylaspartates via β-lactone ring opening
Armstrong, Alan,Geldart, Stephen P.,Jenner, Chloe R.,Scutt, James N.
, p. 8091 - 8094 (2008/02/13)
(Chemical Equation Presented) Cinchona alkaloid-catalyzed reaction of ethyl glyoxylate with substituted ketenes, formed in situ, gives disubstituted β-lactones in moderate yield and high enantiomeric excess. Subsequent azide ring opening, reduction, and e
SYNTHESIS AND ABSOLUTE STEREOCHEMISTRY OF SERRICORNIN
Mori, Kenji,Nomi, Hiroko,Chuman, Tatsuji,Kohno, Masahiro,Kato, Kunio,Noguchi, Masao
, p. 3705 - 3712 (2007/10/02)
The absolute stereochemistry of serricornin (4,6-dimethyl-7-hydroxy-3-nonanone) was established as 4S, 6S, 7S by synthesizing both (4S, 6S, 7S)-isomer and its antipode.Only the natural enantiomer was bioactive.by