α‐Substitution Effects on the Ease of  S → N ‐Acyl Transfer in Aminothioesters | Zendy

ElGendy Bahaa ElDien M. | Zendy; Ghazvini Zadeh Ebrahim H. | Zendy; Sotuyo Ania C. | Zendy; Pillai Girinath G. | Zendy; Katritzky Alan R. | Zendy

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α‐Substitution Effects on the Ease of S → N ‐Acyl Transfer in Aminothioesters

Author(s) -

ElGendy Bahaa ElDien M.,

Ghazvini Zadeh Ebrahim H.,

Sotuyo Ania C.,

Pillai Girinath G.,

Katritzky Alan R.

Publication year - 2013

Publication title -

chemical biology and drug design

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.59

H-Index - 77

eISSN - 1747-0285

pISSN - 1747-0277

DOI - 10.1111/cbdd.12092

Subject(s) - thioester , chemistry , quantum chemical , amine gas treating , stereochemistry , acyl group , acylation , group (periodic table) , molecule , organic chemistry , enzyme , catalysis

In S ‐acylcysteines and homocysteines, the efficacy and rate of S → N ‐acyl transfer (5 and 6 cyclic TSs) vary with the size of S ‐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, NH 2 ) substituents.

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