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191140

Sigma-Aldrich

7-Aminocephalosporanic acid

98%

Synonym(s):

7-ACA

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About This Item

Empirical Formula (Hill Notation):
C10H12N2O5S
CAS Number:
957-68-6
Molecular Weight:
272.28
Beilstein/REAXYS Number:
622637
EC Number:
213-485-0
MDL number:
MFCD00005177
UNSPSC Code:
12352106
PubChem Substance ID:
24851470
NACRES:
NA.22

Quality Level

200

assay

98%

form

powder

optical activity

[α]19/D +90°, c = 0.5 in KH2PO4/trace NaOH

reaction suitability

reaction type: solution phase peptide synthesis

mp

>300 °C (lit.)

antibiotic activity spectrum

Gram-positive bacteria

application(s)

peptide synthesis

mode of action

cell wall synthesis | interferes

storage temp.

2-8°C

SMILES string

[H][C@]12SCC(COC(C)=O)=C(N1C(=O)[C@H]2N)C(O)=O

InChI

1S/C10H12N2O5S/c1-4(13)17-2-5-3-18-9-6(11)8(14)12(9)7(5)10(15)16/h6,9H,2-3,11H2,1H3,(H,15,16)/t6-,9-/m1/s1

InChI key

HSHGZXNAXBPPDL-HZGVNTEJSA-N

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General description

Chemical structure: ß-lactam

Application

7-Aminocephalosporanic acid (7-ACA) can be used as a starting material to synthesize:
  • Cefotaxime by acylation reaction with S-benzothiazol-2-yl(2-amino-4-thiazolyl)(methoxyimino)thioacetate (MAEM) in the presence of triethylamine.
  • Cefpodoxime proxetil, a third-generation antibiotic via cefotaxime intermediate.
  • Sodium 3′-substituted cephalosporanate sulfone derivatives as potential inhibitors of β-lactamase.

Potent inhibitor of bacterial (S. aureus) β-lactamase.

pictograms

Health hazard
GHS08

signalword

Danger

Hazard Classifications

Resp. Sens. 1 - Skin Sens. 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Denis L Atroshenko et al.
International journal of molecular sciences, 20(18) (2019-09-11)
d-amino acid oxidase (DAAO, EC 1.4.3.3) is used in many biotechnological processes. The main industrial application of DAAO is biocatalytic production of 7-aminocephalosporanic acid from cephalosporin C with a two enzymes system. DAAO from the yeast Trigonopsis variabilis (TvDAAO) shows
Cosmin Butnarasu et al.
International journal of pharmaceutics, 564, 136-144 (2019-04-17)
Mucin is a complex glycoprotein consisting of a wide variety of functional groups that can interact with exogenous agents. The binding to mucin plays a crucial role in drug pharmacokinetics especially in diseases, such as cystic fibrosis (CF), where mucin
Synthesis and Preliminary Biological Evaluation of 3?-Substituted Cephem Sulfones as Potential β-Lactamase Inhibitors
De Angelis F, et al.
European Journal of Organic Chemistry, 2001(16), 3075-3081 (2001)
Zhanglin Lin et al.
Biotechnology and bioengineering, 117(10), 2923-2932 (2020-06-17)
Site-directed protein immobilization allows the homogeneous orientation of proteins with high retention of activity, which is advantageous for many applications. Here, we report a facile, specific, and efficient strategy based on the SpyTag-SpyCatcher chemistry. Two SpyTag-fused model proteins, that is
Irene Martínez-Martínez et al.
Analytical biochemistry, 369(2), 210-217 (2007-07-27)
A bromothymol blue-based colorimetric assay has been devised to screen for acetyl xylan esterase or cephalosporin C (CPC) deacetylase activities using 7-amino cephalosporanic acid (7-ACA), CPC, or acetylated xylan as substrate. These enzymes are not screened with their natural substrates
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