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Merck
CN

A1005

(+)-6-Aminopenicillanic acid

Synonym(s):

(2S,5R,6R)-6-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-APA

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About This Item

Empirical Formula (Hill Notation):
C8H12N2O3S
CAS Number:
551-16-6
Molecular Weight:
216.26
EC Number:
208-993-4
UNSPSC Code:
12352200
MDL number:
MFCD00005176
Beilstein/REAXYS Number:
15080

Key Documents

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mp

198-200 °C (dec.) (lit.)

mode of action

cell wall synthesis | interferes

storage temp.

2-8°C

SMILES string

CC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(O)=O

InChI

1S/C8H12N2O3S/c1-8(2)4(7(12)13)10-5(11)3(9)6(10)14-8/h3-4,6H,9H2,1-2H3,(H,12,13)/t3-,4+,6-/m1/s1

InChI key

NGHVIOIJCVXTGV-ALEPSDHESA-N

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General description

Chemical structure: β-lactam

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H319

Hazard Classifications

Eye Irrit. 2

Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
127H3424
094H3467
087F3530
085H3465
045H2501

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Louis Anthony Tony Cox et al.
Risk analysis : an official publication of the Society for Risk Analysis, 29(6), 796-805 (2009-06-06)
Penicillin and ampicillin drugs are approved for use in food animals in the United States to treat, control, and prevent diseases, and penicillin is approved for use to improve growth rates in pigs and poultry. This article considers the possibility
Junqi Zhao et al.
Bioresource technology, 102(2), 529-535 (2010-10-23)
In this study, macro-mesoporous silica spheres were prepared with a micro-device and used as the support for the immobilization of penicillin G acylase (PGA). To measure the enzymatic activity, the silica spheres with immobilized PGA were placed into a packed-bed
Ye-Wang Zhang et al.
Applied microbiology and biotechnology, 88(1), 49-55 (2010-06-23)
A one-pot, two-step enzymatic synthesis of amoxicillin from penicillin G, using penicillin acylase, is presented. Immobilized penicillin acylase from Kluyvera citrophila was selected as the biocatalyst for its good pH stability and selectivity. Hydrolysis of penicillin G and synthesis of
Joanna Skiba et al.
European journal of medicinal chemistry, 57, 234-239 (2012-10-18)
We report on the synthesis of ferrocenyl-ampicillin and ferrocenyl-6-aminopenicillinic acid bioconjugates. Title compounds were characterized by (1)H NMR, IR, MS and elemental analysis. These novel ferrocenyl-antibiotic conjugates were also investigated by cyclic voltammetry (CV). Ferrocenyl-ampicillin complexes revealed reversible uncomplicated oxidation
A K Dolui et al.
Indian journal of experimental biology, 49(4), 289-292 (2011-05-28)
In the present study different bacterial samples were isolated from soil of different places of Dibrugarh and screened for biotransformation ability to produce 6-Aminopenicillanic acid. Among ten isolated bacterial samples, three gram positive bacterial samples designated as AKDD-2, AKDD-4 and
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