85466-66-6Relevant articles and documents
Structure-Activity Relationship Study of Majusculamides A and B and Their Analogues on Osteogenic Activity
Nakajima, Daisuke,Natsume, Noriyuki,Ozaki, Kaori,Teruya, Toshiaki,Yokoshima, Satoshi
, p. 2477 - 2482 (2020/10/02)
We discovered that majusculamide A (1) and majusculamide B (2), isolated from a marine cyanobacterium collected in Okinawa, induced osteoblast differentiation in MC3T3-E1 cells. Although majusculamide A (1) has a different configuration only at the C-19 stereocenter, bearing a methyl group, compared to majusculamide B (2), the effect of 1 was stronger than that of 2. We synthesized some analogues of the majusculamides (3-15) and evaluated osteogenic activities of these analogues. The structure-activity relationship study of majusculamide analogues suggested that the number of methyls and configuration at C-19 and the nature of the substituent at C-20 of majusculamide A (1) may be important for the osteoblast differentiation-inducing effect of 1.
Iridium-Catalyzed Asymmetric Hydrogenation of N-Alkyl α-Aryl Furan-Containing Imines: an Efficient Route to Unnatural N-Alkyl Arylalanines and Related Derivatives
Mazuela, Javier,Antonsson, Thomas,Knerr, Laurent,Marsden, Stephen P.,Munday, Rachel H.,Johansson, Magnus J.
supporting information, p. 578 - 584 (2018/12/11)
High throughput experimentation (HTE) has enabled the rapid identification of ligand/precatalyst combinations that facilitate highly enantioselective hydrogenations of prochiral N-alkyl α-aryl ketimines containing a furyl moiety. The chiral amines obtained have proven to be modular precursors in the synthesis of unnatural mono N-alkylated arylalanines and related derivatives. (Figure presented.).
Total syntheses of cathepsin D inhibitory izenamides A, B, and C and structural confirmation of izenamide B
Lim, Changjin
, (2019/10/02)
The first total syntheses of izenamides A, B, and C, which are depsipeptides inhibitor of cathepsin D, were accomplished. In addition, the stereochemistry of izenamide B was confirmed by our syntheses. The key features of our synthetic route involve the avoidance of critical 2,5-diketopiperazine (DKP) formation and the minimization of epimerization during the coupling of amino acids for the target peptides.
Gram-Scale Solution-Phase Synthesis of Heptapeptide Side Chain of Teixobactin 1
Chandrasekhar, Srivari,Donikela, Sangeetha,Mainkar, Prathama S.,Nayani, Kiranmai,Nomula, Vishnuvardhan
supporting information, p. 2268 - 2272 (2019/12/11)
We report herein a scalable synthesis of linear heptapeptide side chain of the depsipeptide natural product teixobactin through solution phase. The synthesis of heptapeptide was achieved through an efficient coupling of suitably protected tripeptide and tetrapeptide comprising of three d-amino acids and four usual l-amino acid subunits.
D-amino acid position influences the anticancer activity of galaxamide analogs: An apoptotic mechanism study
Bai, Defa,Yu, Siming,Zhong, Shenghui,Zhao, Bingxin,Qiu, Shaoling,Chen, Jianwei,Lunagariya, Jignesh,Liao, Xiaojian,Xu, Shihai
, (2017/03/20)
Galaxamide, an extract from Galaxaura filamentosa, is a cyclic pentapeptide containing five L-leucines. Due to the particular cyclic structure and the excellent anticancer activity, synthesis of Galaxamide and its analogs and their subsequent bio-applications have attracted great attention. In the present work, we synthesized six Galaxamide analogs by replacing one of the L-leucines with phenylalanine and varying the D-amino acid position. The anticancer effect of the synthesized Galaxamide analogs was tested against four in vitro human cancer cell lines, human hepatocellular cells (HepG2), human breast cancer cell (MCF-7), human breast adenocarcinoma cells (MDA-MB-435) and a human cervical carcinoma cell line (Hela). Results showed that Galaxamide analogs with differentD-amino acid positions displayed distinct anticancer potential. The Galaxamide analog containing D-amino acid at position 5 (Analog-6) presented the strongest anticancer activity. The mechanism study revealed that Analog-6 could cause the early apoptosis of HepG2 cells by inhibiting their growth in the sub-G1 stage of the cell cycle and induce the chromatin condensation and fragmentation, which can be seen as 68% of HepG2 cells inhibited in the sub-G1 stage. Moreover, a mitochondria-mediated pathway was found to be involved in the apoptotic process of Analog-6 on HepG2 cells.
Synthetic studies toward (+)-spongidepsin
Venkateswar Reddy, Guvvala,Satish Chandra Kumar, Rotte,Shankaraiah, Gundeti,Suresh Babu, Katragadda,Madhusudana Rao, Janaswamy
, p. 1590 - 1600 (2013/09/02)
A convergent enantiomerically controlled synthetic effort toward (+)-spongidepsin is reported. The synthesis benefits from the use of readily available and inexpensive starting materials like D-mannitol and (-)-β-citronellene. Key transformations include Evans asymmetric methylation, Mitsunobu esterification, (1H-benzotriazol-1-yloxy) tripyrrolidinophosphonium hexafluorophosphate (PyBOP)-mediated amide formation for the preparation of a fully functionalized acyclic precursor, and ring-closing metathesis (RCM). Copyright
Isolation of ciliatamide D from a marine sponge Stelletta sp. and a reinvestigation of the configuration of ciliatamide A
Imae, Yasufumi,Takada, Kentaro,Okada, Shigeru,Ise, Yuji,Yoshimura, Hiroshi,Morii, Yasuhiro,Matsunaga, Shigeki
, p. 755 - 758 (2013/06/05)
A new lipopeptide, ciliatamide D (1), was isolated from a marine sponge Stelletta sp., collected at Oshimashinsone, together with the known compound ciliatamide A (2). Ciliatamide D (1) is a congener of 2, in which N-Me-Phe is replaced by N-Me-Met(O). Marfey's analysis of the acid hydrolysate of 1 demonstrated that the two constituent amino acids were both in the l-form. This result prompted us to carefully investigate the configuration of 2, resulting in the assignment of the l-form for both residues.
Highly practical methodology for the synthesis of D- and L-α-amino acids, N-protected α-amino acids, and N-methyl-α-amino acids
Myers, Andrew G.,Gleason, James L.,Yoon, Taeyoung,Kung, Daniel W.
, p. 656 - 673 (2007/10/03)
Full details are provided for an exceedingly practical method to synthesize D- and L-α-amino acids, N-protected α-amino acids, and N-methyl-α-amino acids, employing as a key step the asymmetric alkylation of pseudoephedrine glycinamide (1) or pseudoephedrine sarcosinamide (2). Practical procedures for the synthesis of 1 and 2 from pseudoephedrine and glycine methyl ester or sarcosine methyl ester, respectively, are presented. Optimum protocols for the enolization and subsequent alkylation of 1 and 2 are described. Alkylation reactions of 1 and 2 are found to be quite efficient with a wide range of alkyl halide substrates, and the products are formed with high diastereoselectivity. The products of these alkylation reactions are hydrolyzed efficiently and with little to no racemization simply by heating in water or water-dioxane mixtures. This protocol provides an exceedingly practical method for the preparation of salt-free α-amino acids of high enantiomeric purity. Alternatively, the alkylation products may be hydrolyzed in high yield and with little to no racemization by heating with aqueous sodium hydroxide. The alkaline hydrolyzate can then be treated with an acylating reagent to provide directly highly enantiomerically enriched N-protected derivatives such as N-Boc and N-Fmoc. Key features necessary for the successful execution of these experimental procedures are identified.
