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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:
622637
EC Number:
213-485-0
MDL number:
MFCD00005177
UNSPSC Code:
12352106
PubChem Substance ID:
24851470
NACRES:
NA.22

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

Signal Word

Danger

Hazard Statements

H317,H334

Hazard Classifications

Resp. Sens. 1 - Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, 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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Dongxue Hu et al.
Bioresource technology, 304, 123014-123014 (2020-02-24)
In this study, a lab-scale multiple draft tubes airlift loop membrane bioreactor (Mt-ALMBR) was used for treating acidic 7-amino cephalosporanic acid (7-ACA) wastewater under different pHs (3.54-6.20) and hydraulic retention time (HRT) (48 h, 36 h, 24 h and 16 h). During about 200 days
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
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
Iskandar Dib et al.
Biotechnology and bioengineering, 94(4), 645-654 (2006-03-16)
Trigonopsis variabilis D-amino acid oxidase (TvDAO) is a long-known flavoenzyme whose most important biocatalytic application is currently the industrial production of 7-amino-cephalosporanic acid (7-ACA) from cephalosporin C. Lacking mechanistic foundation, rational stabilization of TvDAO for improved process performance remains a
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