6-aminopenicillanic acid

6-アミノペニシラン酸

WordNet

1. street name for lysergic acid diethylamide (同)back breaker, battery-acid, dose, dot, Elvis, loony toons, Lucy in the sky with diamonds, pane, superman, window pane, Zen
2. any of various water-soluble compounds having a sour taste and capable of turning litmus red and reacting with a base to form a salt
3. having the characteristics of an acid; "an acid reaction"

PrepTutorEJDIC

1. 酸性の / 酸味のある,すっぱい(sour) / (言葉・態度などが)厳しい,しんらつな / 酸 / すっぱいもの / 《俗》=LSD

Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/02/23 16:50:27」(JST)

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6-Aminopenicillanic acid
IUPAC name (2S,5R,6R)-6-Amino-3,3-dimethyl-7-oxo-4- thia-1-azabicyclo[3.2.0]heptane-2- carboxylic acid
Identifiers
CAS number	551-16-6 Y
PubChem	11082
ChemSpider	10611 Y
ChEBI	CHEBI:57869 Y
Jmol-3D images	Image 1
SMILES O=C(O)[C@@H]1N2C(=O)[C@@H](N)[C@H]2SC1(C)C
InChI 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 Y Key: NGHVIOIJCVXTGV-ALEPSDHESA-N Y InChI=1/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 Key: NGHVIOIJCVXTGV-ALEPSDHEBW
Properties
Molecular formula	C8H12N2O3S
Molar mass	216.25 g/mol
Melting point	198 - 200 °C
Boiling point	> 200 °C (decomposes)
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

6-APA is the chemical compound (+)-6-aminopenicillanic acid.

Use

6-APA is the core of penicillins. It is obtained from the fermentation brew of the Penicillium mold and used as the main starting block for the preparation of numerous semisynthetic penicillins.

Manufacture

This useful compound can be made enzymatically, or chemically as follows, starting from penicillin G:

Weissenburger, H. W. O.; Van der Hoven, M. G.; Recl. Trav. Chim. Pays-Bas 1970, 89, 1081.

History

In 1958, Beecham scientists in the UK discovered the penicillin nucleus, 6-APA. From that starting material, a large number of new semisynthetic penicillins could be designed, whose activity was directed against problem infections.

References

External links

• US patent 2,941,995 on espacenet

See also

• 7-ACA

UpToDate Contents

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English Journal

• In vivo kinetic analysis of the penicillin biosynthesis pathway using PAA stimulus response experiments.

• Deshmukh AT1, Verheijen PJ1, Maleki Seifar R1, Heijnen JJ1, van Gulik WM2.
• Metabolic engineering.Metab Eng.2015 Nov;32:155-73. doi: 10.1016/j.ymben.2015.09.018. Epub 2015 Oct 19.
• In this study we combined experimentation with mathematical modeling to unravel the in vivo kinetic properties of the enzymes and transporters of the penicillin biosynthesis pathway in a high yielding Penicillium chrysogenum strain. The experiment consisted of a step response experiment with the sid
• PMID 26476338

• Comparison of binding behavior for molecularly imprinted polymers prepared by hierarchical imprinting or Pickering emulsion polymerization.

• Giovannoli C1, Passini C1, Anfossi L1, Nardo FD1, Spano G1, Maurino V1, Baggiani C1.
• Journal of separation science.J Sep Sci.2015 Oct;38(20):3661-8. doi: 10.1002/jssc.201500511. Epub 2015 Sep 9.
• The aim of this study was the evaluation of the binding performances and selectivity of molecularly imprinted beads prepared toward several penicillins (i) by hierarchical bulk polymerization in the pores of template-grafted silica microbeads (hMIPs) and (ii) by Pickering emulsion polymerization in
• PMID 26249317

• Efficient enzymatic synthesis of ampicillin by mutant Alcaligenes faecalis penicillin G acylase.

• Deng S1, Su E2, Ma X1, Yang S1, Wei D3.
• Journal of biotechnology.J Biotechnol.2015 Apr 10;199:62-8. doi: 10.1016/j.jbiotec.2015.01.004. Epub 2015 Feb 11.
• Semi-synthetic β-lactam antibiotics (SSBAs) are one of the most important antibiotic families in the world market. Their enzymatic synthesis can be catalyzed by penicillin G acylases (PGAs). In this study, to improve enzymatic synthesis of ampicillin, site-saturating mutagenesis was performed on th
• PMID 25681630

Japanese Journal

• THE NEW CONVENIENT SYNTHESIS OF NOVEL γ-ALKYLIDENEBUTENOLIDES FROM 6-AMINOPENICILLANIC ACID

• Yu Bin,Zhang En,Fang Yuan [他]
• Heterocycles : an international journal for reviews and communications in heterocyclic chemistry 87ﾏﾏ(1), 163-176, 2013-01-01
• NAID 40019530804

• Purification and Characterization of Inducible Cephalexin Synthesizing Enzyme in Gluconobacter oxydans

• , , [他], ,
• Bioscience, biotechnology, and biochemistry 69(3), 463-469, 2005-03-23
• … The enzyme had maximal activity around pH 6.0 to 6.5, and this activity was thermally stable up to 40 °C. … Synthesis of cephalexin from D-phenylglycine methyl ester and 7-amino-3-deacetoxycephalosporanic acid (7-ADCA) by the purified CSE was demonstrated. … Apart from cephalexin, ampicillin was also synthesized by the purified CSE from its acyl precursors and 6-aminopenicillanic acid (6-APA). …
• NAID 130000030382

• Adsorptive Interaction of Certain Beta-lactam Antibiotics in Aqueous Solution: Interpretation by Frontier Orbital Theory

• , ,
• Journal of chemical engineering of Japan 33(2), 303-307, 2000-04
• … The adsorption of certain beta-lactam antibiotics such as 7-aminocephalosporanic acid, 7-aminodeacetoxy cephalosporanic acid, cephalexin, cefadroxyl, cephalosporin-C, and 6-aminopenicillanic acid in aqueous solution is studied using two different types of polymeric resins and activated carbon as the adsorbents. …
• NAID 130000020415

Related Links

• 6-Aminopenicillanic Acid 551-16-6 | 東京化成工業株式会社

[6-Aminopenicillanic Acid] [551-16-6] ... 別名 (英名), 6-Amino-3,3-dimethyl-7-oxo- 4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid. 別名 (英名), 6-APA. 和名, 6- アミノペニシラン酸. 和名別名, 6-アミノ-3,3-ジメチル-7-オキソ-4-チア-1- ...

Related Pictures

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★リンクテーブル★

リンク元	「6-アミノペニシラン酸」

「6-アミノペニシラン酸」

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英

6-aminopenicillanic acid, 6-APA