7-β-Thien-2-yl-acetamido-3-[(4-nitro-3-carboxyphenyl) thiomethyl]-3-cephem-4-carboxylic acid (CENTA) is a yellow chromogenic β-lactamases (BL) substrate. It hydrolyses readily in the presence of all BL and is therefore suitable for kinetic studies, the detection of BL enzymes in crude extracts and chromatographic fractions. CENTA is commercially available at a high price because of the cumbersome synthetic protocol, the only currently available for its preparation. Here we describe a new efficient and improved process for the preparation of CENTA. Starting from the easily available 7-aminocephalosporanic acid (7-ACA) through a three-step synthesis, CENTA was obtained with a 75% overall yield. The newly developed process proceeds through a pivotal intermediate in cephalosporin chemistry, which may be used as starting compound for the development of new cephalosporin derivatives.

An Improved Synthesis of CENTA, a Chromogenic Substrate for β-Lactamases / QUOTADAMO, ANTONIO; LINCIANO, PASQUALE; DAVOLI, Paolo; TONDI, Donatella; COSTI, Maria Paola; VENTURELLI, Alberto. - In: SYNLETT. - ISSN 0936-5214. - ELETTRONICO. - 27:17(2016), pp. 2447-2450. [10.1055/s-0035-1562454]

An Improved Synthesis of CENTA, a Chromogenic Substrate for β-Lactamases

QUOTADAMO, ANTONIO
Investigation
;
LINCIANO, PASQUALE
Investigation
;
DAVOLI, Paolo
Data Curation
;
TONDI, Donatella
Writing – Review & Editing
;
COSTI, Maria Paola
Supervision
;
VENTURELLI, Alberto
2016

Abstract

7-β-Thien-2-yl-acetamido-3-[(4-nitro-3-carboxyphenyl) thiomethyl]-3-cephem-4-carboxylic acid (CENTA) is a yellow chromogenic β-lactamases (BL) substrate. It hydrolyses readily in the presence of all BL and is therefore suitable for kinetic studies, the detection of BL enzymes in crude extracts and chromatographic fractions. CENTA is commercially available at a high price because of the cumbersome synthetic protocol, the only currently available for its preparation. Here we describe a new efficient and improved process for the preparation of CENTA. Starting from the easily available 7-aminocephalosporanic acid (7-ACA) through a three-step synthesis, CENTA was obtained with a 75% overall yield. The newly developed process proceeds through a pivotal intermediate in cephalosporin chemistry, which may be used as starting compound for the development of new cephalosporin derivatives.
2016
7-lug-2016
27
17
2447
2450
An Improved Synthesis of CENTA, a Chromogenic Substrate for β-Lactamases / QUOTADAMO, ANTONIO; LINCIANO, PASQUALE; DAVOLI, Paolo; TONDI, Donatella; COSTI, Maria Paola; VENTURELLI, Alberto. - In: SYNLETT. - ISSN 0936-5214. - ELETTRONICO. - 27:17(2016), pp. 2447-2450. [10.1055/s-0035-1562454]
QUOTADAMO, ANTONIO; LINCIANO, PASQUALE; DAVOLI, Paolo; TONDI, Donatella; COSTI, Maria Paola; VENTURELLI, Alberto
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11380/1116430
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