|1Shilin, SV, 1Shablykina, OV, 1Ishchenko, VV, 1Khylia, VP |
1Taras Shevchenko National University of Kyiv
|Dopov. Nac. akad. nauk Ukr. 2017, 1:82-87|
The relative reactivities of (isocoumarin-3-yl)- and (3,4-dihydroisocoumarin-3-yl)phenoxyacetic acids in the synthesis of amino acid derivatives, which includes the activated N-hydroxysuccinimide esters producing, are studied. It is found that, for the compounds with unsaturated isocoumarin cycle, the rate of activated ester formation is significantly reduced, when a substituent (regardless of size) in the ortho position to the oxyacetic acid fragment appears. While the slowing interaction of their saturated analogues with N-hydroxysuccinimide is not observed due to the presence of the ortho substituent.
|Keywords: (3, (isocoumarin-3-yl)phenoxyacetic acids, 4-dihydroisocoumarin-3-yl)phenoxyacetic acids, activated ester method, amino acid derivatives, N-hydroxysuccinimide|
1. Hill R.A. Naturally occurring isocoumarins, Progress in the Chemistry of Organic Natural Products, Vol. 49, Vienna: Springer, 1986, https://doi.org/10.1007/978-3-7091-8846-0.
2. Shilin S.V., Shablykina O.V., Ishchenko V.V., Khilya V.P. Chem. Nat. Compd., 2014, 50, Iss. 4: 638—643, https://doi.org/10.1007/s10600-014-1042-5.
3. Shilin S.V., Shablykina O.V., Zabolotnaya Yu.N., Ishchenko V.V., Khylia V.P. Khimiya prirodn. soyedin., 2016, No 4: 516—521 (in Russian).
4. Hershkovich A.A., Kibyrev V.K. Chemical synthesis of peptides, Kiev: Naukova Dumka, 1992 (in Russian).
5. Anderson G. W., Zimmerman J. E., Callahan F. M. J. Am. Chem. Soc., 1963, 85: 3039, https://doi.org/10.1021/ja00902a047
6. Ishchenko V.V., Voevoda N.M., Shablykina O.V., Turov A.V., Khilya V.P. Chem. Heterocycl. Comp., 2012, 47, No 10: 1212—1224, https://doi.org/10.1007/s10593-013-1183-7.