899900-52-8Relevant articles and documents
Ochraceopetalin, a mixed-biogenetic salt of polyketide and amino acid origins from a marine-derived aspergillus ochraceopetaliformis fungus
Park, Sung Chul,Lee, Jung-Ho,Hwang, Ji-Yeon,Kwon, Oh-Seok,Liao, Lijuan,Oh, Dong-Chan,Oh, Ki-Bong,Shin, Jongheon
, (2021/08/16)
Ochraceopetalin (1), a mixed-biogenetic salt compound and its component 2 were isolated from the culture broths of a marine-derived fungus, Aspergillus ochraceopetaliformis. Based on combined spectroscopic and chemical analyses, the structure of 1 was determined to be a sulfonated diphenylether-aminol-amino acid ester guanidinium salt of an unprecedented structural class, while 2 was determined to be the corresponding sulfonated diphenylether. Ochraceopetaguanidine (3), the other guanidine-bearing aminol amino acid ester component, was also prepared and structurally elucidated. Compound 1 exhibited significant cytotoxicity against K562 and A549 cells.
Heptavalinamide A, an Extensively N-Methylated Linear Nonapeptide from a Cyanobacterium Symploca sp. And Development of a Highly Sensitive Analysis of N, N-Dimethylvaline by LCMS
Itoi, Shiro,Matsunaga, Shigeki,Oikawa, Hiroshi,Sugita, Haruo,Suo, Rei,Suzuki, Toshiyuki,Takada, Kentaro,Watanabe, Ryuichi
supporting information, (2020/02/22)
An extensively N-methylated linear nonapeptide heptavalinamide A (1) was isolated from the marine cyanobacterium Symploca sp. collected at Kabira Reef of Ishigaki Island, Okinawa. The amino acid sequence of 1 was assigned by interpretation of 2D NMR and MS/MS data. The absolute configurations of the constituent amino acids were determined by the application of Marfey's method. A method to assign the configuration of N,N-dimethylvaline by LCMS is discussed.
Defining the structural parameters that confer anticonvulsant activity by the site-by-site modification of (R)-N′-benzyl 2-amino-3-methylbutanamide
King, Amber M.,De Ryck, Marc,Kaminski, Rafal,Valade, Anne,Stables, James P.,Kohn, Harold
supporting information; experimental part, p. 6432 - 6442 (2011/12/01)
Primary amino acid derivatives (PAADs) (N′-benzyl 2-substituted 2-amino acetamides) are structurally related to functionalized amino acids (FAAs) (N′-benzyl 2-substituted 2-acetamido acetamides) but differ by the absence of the terminal N-acetyl group. Both classes exhibit potent anticonvulsant activities in the maximal electroshock seizure animal model, and the reported structure-activity relationships (SARs) of PAADs and FAAs differ in significant ways. Recently, we documented that PAAD efficacy was associated with a hydrocarbon moiety at the C(2)-carbon, while in the FAAs, a substituted heteroatom one atom removed from the C(2)-center was optimal. Previously in this issue, we showed that PAAD activity was dependent upon the electronic properties of the 4′-N′-benzylamide substituent, while FAA activity was insensitive to electronic changes at this site. In this study, we prepared analogues of (R)-N′-benzyl 2-amino-3-methylbutanamide to identify the structural components for maximal anticonvulsant activity. We demonstrated that the SAR of PAADs and FAAs diverged at the terminal amide site and that PAADs had considerably more structural latitude in the types of units that could be incorporated at this position, suggesting that these compounds function according to different mechanism(s).