27920-90-7

Basic information

• Product Name: glutaryl-7-aminocephalosporanic acid
• Synonyms: glutaryl-7-aminocephalosporanic acid;(7R)-7-(4-carboxybutanamido)cephalosporanic acid
• CAS NO: 27920-90-7
• Molecular Formula: C₁₅H₁₈N₂O₈S
• Molecular Weight: 386.38
• Mol File: 27920-90-7.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 803.3°Cat760mmHg
• Flash Point: 439.6°C
• Appearance: /
• Density: 1.56g/cm³
• Vapor Pressure: 2.42E-28mmHg at 25°C
• Refractive Index: 1.631
• PKA: 2.68±0.50(Predicted)
• CAS DataBase Reference: glutaryl-7-aminocephalosporanic acid(CAS DataBase Reference)
• NIST Chemistry Reference: glutaryl-7-aminocephalosporanic acid(27920-90-7)
• EPA Substance Registry System: glutaryl-7-aminocephalosporanic acid(27920-90-7)

Safety Data

• Hazardous Substances Data: 27920-90-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C15H18N2O8S/c1-7(18)25-5-8-6-26-14-11(13(22)17(14)12(8)15(23)24)16-9(19)3-2-4-10(20)21/h11,14H,2-6H2,1H3,(H,16,19)(H,20,21)(H,23,24)/t11-,14-/m1/s1

Upstream product

• 108-24-7 acetic anhydride 
• 108-55-4 glutaric anhydride, 
• 957-68-6 7-Aminocephalosporanic acid 
• 61-24-5 cephalosporin C 

Downstream Products

• 957-68-6 7-Aminocephalosporanic acid 
• 110-94-1 1,5-pentanedioic acid 
• 29120-98-7 (6R,7R)-3-Acetoxymethyl-7-(4-carboxybutanamido)ceph-3-em-4-carboxylic acid bis diphenylmethyl ester 

Relevant articles and documents

Aqueous acetylation of desacetyl glutaryl 7-amino-cephalosporanic acid (7ACA) and speculation on the origin of desacetyl cephalosporin C in fermentation broth

Acetylation of desacetyl glutaryl 7-aminocephalosporanic acid (7ACA), an intermediate in the two-stage enzymatic cleavage of cephalosporin C, has been accomplished in aqueous media with acetic anhydride. Because the reaction is done in water, conversion of desacetyl glutaryl 7ACA to glutaryl 7ACA can be accomplished at an early stage in the purification process. Evidence is presented that desacetyl cephalosporin C in cephalosporin C broth is formed from the mycelial catalyzed hydrolysis of cephalosporin C.

One-pot conversion of cephalosporin C to 7-aminocephalosporanic acid in the absence of hydrogen peroxide

The main drawback in the production of 7-aminocephalosporanic acid (7-ACA) at the industrial level is the inactivation of the enzymes implicated in the process due to the presence of hydrogen peroxide during the reaction. As an alternative, we have developed the conversion of cephalosporin C to 7-ACA in a single reactor without the presence of hydrogen peroxide during the reaction, achieving more than 80% yield. In order to develop this process, D-amino acid oxidase (DAAO) was co-immobilized with catalase (CAT), which is able to fully eliminate in situ the hydrogen peroxide formed by the neighbouring DAAO molecules. Thus, the product of the reaction is only α-ketoadipyl-7-ACA. This system prevents the inactivation of the oxidase by hydrogen peroxide, solving the main problem of the enzymatic process. Moreover, we have found that α-ketoadipyl-7-ACA is recognized as a substrate by glutaryl acylase (GAC) and hydrolyzed as long as glutaric acid is absent from the reaction medium (because it is able to inhibit the hydrolysis). The low stability of α-ketoadipyl-7-ACA justifies the use of a single reactor, in which glutaryl acylase is already present when this substrate is generated. Thus, the whole process may (and must) be performed in a single step, and in the absence of hydrogen peroxide that could affect the stabilities of the involved enzymes.