Α‐Substitution Effects on the Ease of S→N‐Acyl Transfer in Aminothioesters. (24th April 2013)

• Record Type: Journal Article
• Authors: El‐Gendy, Bahaa El‐Dien M.; Ghazvini Zadeh, Ebrahim H.; Sotuyo, Ania C.; Pillai, Girinath G.; Katritzky, Alan R.
• Is Part Of: Chemical biology & drug design. Volume 81:Number 5(2013:May)
• Page Start: 577
• Page End: 582
• Publication Date: 2013-04-24
• Subjects: Drugs -- Design -- Periodicals; Pharmaceutical chemistry -- Periodicals; Biochemistry -- Periodicals; 615.19005
• DOI: 10.1111/cbdd.12092
• Languages: English
• ISSNs: 1747-0277

Abstract

<abstract abstract-type="main" xml:lang="en"> <title> <x xml:space="preserve">Abstract</x> </title> <p>In <italic>S</italic>‐acylcysteines and homocysteines, the efficacy and rate of <italic>S</italic>→<italic>N</italic>‐acyl transfer (5 and 6 cyclic TSs) vary with the size of <italic>S</italic>‐acyl group. Conformational and quantum chemical calculations indicate that the spatial distance, b(N‐C), between the terminal amine and the thioester carbon is shortened by α‐C(O)X (X = OH, OMe, NH₂) substituents.</p> </abstract>