768-48-9Relevant articles and documents
Highly Reactive and Tracelessly Cleavable Cysteine-Specific Modification of Proteins via 4-Substituted Cyclopentenone
Yu, Jian,Yang, Xiaoyue,Sun, Yang,Yin, Zheng
supporting information, p. 11598 - 11602 (2018/09/10)
A rapid and cysteine-specific modification of proteins using 4-substituted cyclopentenone via a Michael addition tandem elimination reaction was developed. Compared to the classical method, this reaction featured fast kinetics with a stable product. More importantly, this conjugation could be tracelessly removed by exchange with a Michael addition donor. The conjugation and regeneration process not only exhibited little change to the structures or conformations of the proteins but also exhibited little disturbance to their biological functions, such as their enzymatic activities.
4-Heterosubstituted Cyclopentenone Antiviral Compounds: Synthesis, Mechanism, and Antiviral Evaluation
Mantione, Daniele,Aizpuru, Olatz Olaizola,Memeo, Misal Giuseppe,Bovio, Bruna,Quadrelli, Paolo
, p. 983 - 991 (2016/03/01)
Racemic 4-oxocyclopent-2-en-1-yl acetate was used in a short synthesis of nucleoside analogues with pyrimidine and purine heterobases. The protocol is based on a typical nucleophilic substitution process. Uracil, thymine, 6-chloropurine, and some adenines gave the expected 4-heterosubstituted products along with the isomeric 2-heterosubstituted compounds as minor components. Samples of selected products were evaluated for their antiviral activity in a primary screening against a variety of viruses belonging to different classes. One of the compounds was found to be highly active against human papilloma virus (HPV).
Organic reactions in the solid state: Reactions of enclathrated 3,4- epoxycyclopentanone (= 6-oxobicyclo[3.1.0]hexan-3-one) in Tri-othymotide and absolute configuration of 4-hydroxy- and 4-chlorocyclopent-2-en-1-one
Gerdil, Raymond,Liu, Huiyou,Bernardinelli, Gerald
, p. 418 - 434 (2007/10/03)
Several aspects of the heterogeneous actions of aqueous and gaseous HCl on the chemical behavior of 3,4-epoxycyclopentanone (=6- oxablcyclo[3.1.0]hexan-3-one; 1) included in the asymmetric cages of tri-o- thymotide (TOT) clathrates belonging to space groups P3121 are described, showing specific features strikingly at variance with those observed in liquid solutions. In a first step, the substrate underwent an acid-promoted allylic isomerization, as already observed in our previous investigations, to give optically active 4-hydroxycydopent-2-en-1-one (2). In a Consecutive step, a displacement of the OH group was accomplished by the Cl- anion to afford the corresponding chloro compound 3. Polymorphism was encountered in the preparation of TOT/1 clathrates. Recrystallization of TOT in the pure guest 1 yielded micro-twinned crystals belonging to the P31 space group (host/guest ratio 1: 1), whereas the expected P3121 lattice grew from a mixture of TOT, 1 and MeOH. The structural determination of TOT/1 was carried out by X-ray diffraction (Fig. 1). Kinetic measurements were achieved that shed light on some striking features of this type of heterogeneous reactions for solid-liquid and solid-gas systems. Several reactions of pure clathrate antipodes (+)-TOT/1 with gaseous HCl were carried out under various conditions; concentration and enantiomer-excess(ee) determinations of the products 2 and 3 allowed to establish a larger ee for 3, thus demonstrating the influence of the host-guest diastereomeric association on the progression of the reaction. The correlation of optical activities of the host and products for the global reaction disclosed the sequence (+)-(M)-TOT/1 → (- )-2 → (-)-3. A new way for the preparation of 2 was devised. It was further demonstrated that the X-ray structure analysis of the chiral clathrate (M)- TOT/(+)-2 (Fig. 4) associated with chitoptical measurements was an efficient and straightforward method to determine the absolute (+)-(R)-configuration of the guest. The enantioselectivity of the TOT clathrate for 2 was established by two different methods which allowed the appraisal of an accurate revised value of the specific rotation of 2. The enclathration of 3 occurred exclusively in the orthorhombic centrosymmetric host lattice Pbca, thus prohibiting the X-ray structural determination of the guest absolute configuration. The problem of finding a pathway to the intended enantiomer enrichment of 3 was worked out through the action of aqueous HCI on microcrystalline (+)-TOT/(-)-(S)-2 that gave an optically active mixture of unreacted 2 with 3 as sole product. The pure optically active 3 was isolated by Subsequent TLC. The resolution of 3 was achieved by GC over a chiral column and its (unknown) specific rotation measured. The absolute configuration of 3 was established by the measurement of the enantiomer purity of the optically active mixture 3 obtained after the total conversion of (-)-(S)-2 in the presence of thionyl chloride in Et2O, dioxane, and benzene. It was deduced that the (-)-3 enantiomer had the (S)-configuration.
