Disease relevance of EINECS 213-485-0

• Glutaryl 7-aminocephalosporanic acid acylase of Pseudomonas sp. 130 (C130) was irreversibly inhibited in a time-dependent manner by two substrate analogs bearing side chains of variable length, namely 7beta-bromoacetyl aminocephalosporanic acid (BA-7-ACA) and 7beta-3-bromopropionyl aminocephalosporanic acid (BP-7-ACA) [1].
• New N-substituted 7-aminocephalosporanic acid derivatives as potential agents against Streptococcus pneumoniae. Synthesis and in vitro activity [2].
• Some 7-amino cephalosporanic acid derivatives substituted on the C(7) nitrogen with (S)-and (R)-3-(methyleneaminoxy)-2-methylpropionyl groups were synthesised and tested in vitro for their antimicrobial activity against Gram-positive and Gram-negative bacteria [3].

High impact information on EINECS 213-485-0

• Affinity alkylation of the Trp-B4 residue of the beta -subunit of the glutaryl 7-aminocephalosporanic acid acylase of Pseudomonas sp. 130 [1].
• By contrast, a poor beta-lactamase substrate (7-aminocephalosporanic acid) can fully derepress beta-lactamase expression under conditions where interference of the antibiotic with cell growth is observed [4].
• Glutaryl 7-aminocephalosporanic acid acylase (GCA, EC 3.5.1.11) is a member of N-terminal nucleophile (Ntn) hydrolases [5].
• Our data in a bioreactor indicate an ~90% conversion of cephalosporin C to 7-amino-cephalosporanic acid in a single deacylation step [6].
• The evolved acylase variants we produced are enzymes with a new substrate specificity, not found in nature, and represent a hallmark for industrial production of 7-amino cephalosporanic acid [6].

Chemical compound and disease context of EINECS 213-485-0

• Pseudomonas sp. strain SE83 converts cephalosporin C and 7 beta-(4-carboxybutanamido)cephalosporanic acid (GL-7ACA) to 7-aminocephalosporanic acid (7ACA) [7].
• Pseudomonas strain BL072 produces an acylase enzyme active in hydrolyzing glutaryl-7-aminocephalosporanic acid to 7-aminocephalosporanic acid [8].
• Single-step conversion of cephalosporin-C to 7-aminocephalosporanic acid by free and immobilized cells of Pseudomonas diminuta [9].

Biological context of EINECS 213-485-0

• Abp4 showed broad cross-reaction to human serum albumin (HSA) conjugates of several beta-lactams, 6-aminopenicillanic acid and 7-aminocephalosporanic acid [10].
• Cephalothin: hydrolysis of the C-3'-acetoxy moiety of a 7-aminocephalosporanic acid; observation of both acyl-oxygen bond cleavage and reversible alkyl-oxygen bond cleavage [11].
• Aqueous acetylation of desacetyl glutaryl 7-aminocephalosporanic acid (7ACA) and speculation on the origin of desacetyl cephalosporin C in fermentation broth [12].
• A rapid procedure is reported for the synthesis of cefotaxime, by acylation of the 7-amino cephalosporanic acid with the 2-mercaptobenzothiazolyl thioester of (Z)-2-[2-aminothiazol-4-yl]-2-methoxyimino acetic acid (MAEM) that is a commercial reagent [13].

Associations of EINECS 213-485-0 with other chemical compounds

• The comparative evolution of the absorption spectra, under irradiation at 254 nm, of cefotaxime, thiazoximic acid, and 7-aminocephalosporanic acid shows that it is the delta 3-cephem ring photolysis which gives the yellow color [14].
• Cefamandole nafate is a derivative of 7-aminocephalosporanic acid which has been shown to have good in vitro activity against aerobes traditionally susceptible to cephalosporins as well as many anaerobes, including B. fragilis [15].
• The capacity factors of several penicillins and cephalosporins, as well as those of 7-aminocephalosporanic acid, 6-aminopenicillanic acid, and 7-aminodeacetoxycephalosporanic acid, were determined at pH 2.5-7.5 with different methanol concentrations in the mobile phase [16].
• The anti-cefamandole was easily inhibited in vitro by cefamandole as well as by a variety of related cephalosporins indicating broad cross-reactivity, with the antigenic site primarily the 7-amino-cephalosporanic acid nucleus [17].
• 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 [12].

Gene context of EINECS 213-485-0

• D-amino acid oxidase: its potential in the production of 7-aminocephalosporanic acid [18].

Analytical, diagnostic and therapeutic context of EINECS 213-485-0

• In particular, the mutation to Gln resulted in a high rate of conversion of glutarylcephalosporanic acid to 7-amino-cephalosporanic acid under conditions similar to those of a bioreactor system [19].
• Cephalosporin acylases have application in the production of 7-aminocephalosporanic acid which forms a key raw material for the preparation of semisynthetic injectable cephalosporins [20].

References