Synthesis of a new symmetric carbonate with leaving group

被引:0
|
作者
Segneanu, A. -E. [1 ]
Milea, M. [2 ]
Grozescu, I. [1 ]
机构
[1] Natl Inst Res Dev Electrochem & Condensed Matter, Timisoara 300569, Romania
[2] Polytechn Univ Timisoara, Timisoara 300006, Romania
关键词
Alkoxycarbonyl-type (carbamate) groups; Leaving group; Norbornenyl; racemisation; PEPTIDE-SYNTHESIS;
D O I
暂无
中图分类号
T [工业技术];
学科分类号
08 ;
摘要
The study of the reactivity of organic reactive carbonates with leaving groups (succinimidyl, phthtalimidyl and norbornenyl) towards oxygen and nitrogen nucleophiles proved to be useful due to the applicability of the resulting compounds in avant-garde fields of chemistry, such as biochemistry and the pharmaceutical industry. This study has been heavily focused on developing new, cleaner, chemical processes using an original method. The goal of this paper is to prepare a new symmetrical reactive carbonate with leaving group by an original method, aimed at reducing chemical residues with a negative impact on the environment and human health. In peptide synthesis, reactive organic carbonates are used especially for the protection of amino groups, by converting it into a carbamate-type derivative through an alkoxycarbonylation reaction, and for the activation of carboxyl groups by converting it into a reactive ester. For the protection of the amino function in amino acids, alkoxycarbonyl-type (carbamate) groups are preferred, which minimize the racemization of optically active centers. In modern peptide synthesis, at the international level, the applications of phthtalimidyl organic carbonates are related to the activation of carboxyl groups in amino acids and peptides. The process of obtaining symmetrical carbonate with leaving group is the starting point for obtaining new amino-protecting groups with special importance in the synthesis of peptides.
引用
收藏
页码:197 / 199
页数:3
相关论文
共 50 条
  • [1] A NEW LEAVING GROUP IN ACETOLYSIS REACTIONS - SYNTHESIS OF ALKYL PICRATES
    SINNOTT, ML
    WHITING, MC
    CHEMICAL COMMUNICATIONS, 1968, (24) : 1617 - &
  • [2] Mustard Carbonate Analogues: Influence of the Leaving Group on the Neighboring Effect
    Arico, Fabio
    Aldoshin, Alexander S.
    Tundo, Pietro
    ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2016, 4 (05): : 2843 - 2851
  • [3] Fluorine as a Leaving group in organic Synthesis?
    Wegner, Hermann A.
    NACHRICHTEN AUS DER CHEMIE, 2012, 60 (09) : 880 - 883
  • [4] PYRAZINYLSULFINYL GROUP AS A NEW LEAVING GROUP FOR SULFOXIDE ELIMINATION
    OHTA, A
    SHIMAZAKI, M
    OKIMURA, K
    TONOMURA, Y
    JOURNAL OF PHARMACEUTICAL SCIENCES, 1987, 76 (11) : S148 - S148
  • [5] Glycosylation using diphenylphosphinate as a new leaving group
    Kadokawa, J
    Ebana, J
    Nagaoka, T
    Karasu, M
    Tagaya, H
    Chiba, K
    NIPPON KAGAKU KAISHI, 1999, (09) : 625 - 627
  • [6] AN IMPROVED METHOD FOR OLEFIN SYNTHESIS USING PYRIDYLSELENO GROUP AS A LEAVING GROUP
    TOSHIMITSU, A
    OWADA, H
    UEMURA, S
    OKANO, M
    TETRAHEDRON LETTERS, 1980, 21 (52) : 5037 - 5038
  • [7] BETA-DIETHYLAMINOETHYL GROUP AS A LEAVING GROUP IN KNORR PYRROLE SYNTHESIS
    MIRONOV, AF
    ALARKON, KK
    EVSTIGNE.RP
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1973, (12): : 1643 - 1645
  • [8] USE OF THE BROMOETHYL LEAVING GROUP FOR THE SYNTHESIS OF AN ETHOXYACETYLENEBORONIC ESTER
    MATTESON, DS
    PEACOCK, K
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1964, 2 (02) : 190 - 192
  • [9] Indole: A novel leaving group in the synthesis of oligonucleoside methylphosphonates
    Wang, JC
    Just, G
    TETRAHEDRON LETTERS, 1997, 38 (13) : 2241 - 2244
  • [10] USE OF A NEW FLUORESCENT LEAVING GROUP FOR PROTEASE HISTOCHEMISTRY
    GARRETT, JR
    KYRIACOU, K
    RASNICK, D
    SMITH, RE
    JOURNAL OF HISTOCHEMISTRY & CYTOCHEMISTRY, 1984, 32 (08) : 911 - 911