114525-98-3Relevant academic research and scientific papers
Trimethyl-substituted carbamate as a versatile self-immolative linker for fluorescence detection of enzyme reactions
Inoue, Kazuya,Nakamura, Noriaki,Ojida, Akio,Uchinomiya, Shohei
supporting information, (2020/05/25)
Self-immolative linker is a useful building block of molecular probes, with broad applications in the fields of enzyme activity analysis, stimuli-responsive material science, and drug delivery. This manuscript presents N-methyl dimethyl methyl (i.e., trimethyl) carbamate as a new class of self-immolative linker for the fluorescence detection of enzyme reactions. The trimethyl carbamate was shown to spontaneously undergo intramolecular cyclization upon formation of a carboxylate group, to liberate a fluorophore with the second time rapid reaction kinetics. Interestingly, the auto-cleavage reaction of trimethyl carbamate was also induced by the formation of hydroxyl and amino groups. Fluorescent probes with a trimethyl carbamate could be applicable for fluorescence monitoring of the enzyme reactions catalyzed by esterase, ketoreductase, and aminotransferase, and for fluorescence imaging of intracellular esterase activity in living cells, hence demonstrating the utility of this new class of self-immolative linker.
Nine-Step Total Synthesis and Biological Evaluation of Rhizonin A
Liu, Qingchao,Liu, Langlang,Ratnayake, Ranjala,Luesch, Hendrik,Guo, Yian,Ye, Tao
supporting information, p. 1280 - 1284 (2020/08/05)
We have achieved the total synthesis of an architecturally and biologically intriguing cyclic polypeptide, rhizonin A (1), in an exceptionally concise and convergent fashion. The strategic route entails 9 longest linear steps to elaborate commercially available materials into the natural product with an overall yield of 9.7%. The brevity of sequence and high overall yield was fueled by the judicious selection of chemical tactics. Rhizonin A (1) showed weak inhibitory effects on the cell viability of HCT116 colorectal cancer cells and this activity was dependent on hypoxia-inducible factors.
Synthesis and biological evaluation of analogues of the marine cyclic depsipeptide obyanamide
Zhang, Wei,Ding, Ning,Li, Yingxia
experimental part, p. 533 - 539 (2012/05/04)
On the basis of the total synthesis of obyanamide, 20 analogues of this marine cyclic depsipeptide have been synthesized by (i) preparation of the tripeptide fragments in the western hemisphere using Z/OtBu protocol; (ii) preparation of the dipeptide fragments in the eastern hemisphere using Boc/OMe protocol; and (iii) fragments coupling, removal of protecting groups (Boc and OtBu, in one pot), and macrocyclizaion in the last step. The cytotoxic test showed that three synthetic compounds exhibited moderate activities against HL-60, KB, LOVO, and A549 cell lines. According to the results, the β-amino acid residue was found to play a critical role in the biological activities. Additionally, the ester bond along with the Ala(Thz) moiety was also essential for biological activities. However, it seems too early to draw a conclusion that the N-methylation of Val/Phe can lead to higher or lower cytotoxic activities.
