138488-63-8Relevant articles and documents
Second-generation cycloSal-d4TMP pronucleotides bearing esterase-cleavable sites - The "trapping" concept
Meier, Chris,Ducho, Christian,Jessen, Henning,Vukadinovic-Tenter, Dalibor,Balzarini, Jan
, p. 197 - 206 (2007/10/03)
An extension of the cycloSal-pronucleotide approach is presented. Attachment of an enzyme-cleavable ester/acylal group to the cycloSal-d4TMP triesters should allow these compounds to be trapped intracellularly after cleavage. The ester/acylal groups were introduced in the 3- or 5-position of the cycloSal ring system, and surprising differences were observed in hydrolysis studies in CEM cell extracts with respect to the ester/acylal moiety. While acetyl and levulinyl esters were readily cleaved, alkyl esters of cycloSal-d4TMP acids proved to be resistant to enzymatic cleavage. In contrast, AM-, POM- and POC-acylals were rapidly cleaved in the extracts, leading to cycloSal-d4TMP acids. The antiviral activity of the compounds against HIV is also presented. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
Twisted amides as selective acylating agents for hydroxyl groups under neutral conditions: Models for activated peptides during enzymatic acyl transfer reaction
Yamada, Shinji,Sugaki, Takayuki,Matsuzaki, Kazuhiro
, p. 5932 - 5938 (2007/10/03)
The highly twisted amide 2 served as a selective acylating agent for diols under neutral conditions. The reaction of primary-secondary diols with 2 led to the corresponding primary alkyl monopivalates. For diols containing alcoholic and phenolic hydroxyl groups, alcoholic hydroxyl groups were selectively acylated under neutral conditions, whereas, the opposite selectivity was observed under basic conditions, similar to the cases using acyl halides or acid anhydrides. Although 1 and 3 were unreactive to alcohols, 5-10 having substituent groups at C-4 were reactive to alcohols to give the corresponding acetates or benzoates.