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Ligand 7-aminocephalosporanic acid

Basic Ligand Information

Molecular Structure

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Roles as Enzyme Ligand

In Vivo Product in Enzyme-catalyzed Reactions (4 results)

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Show Natural Product (4 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

3.5.1.93

(7R)-7-(4-carboxybutanamido)cephalosporanate + H2O = (7R)-7-aminocephalosporanate + glutarate

-

-

3.5.1.93

adipyl-7-aminocephalosporanic acid + H2O = 7-aminocephalosporanic acid + adipate

-

-

3.5.1.93

cephalosporin C + H2O = 7-aminocephalosporanic acid + 2-amino-5-hydroxypentanoate

-

-

3.5.1.93

glutaryl-7-aminocephalosporanic acid + H2O = 7-aminocephalosporanic acid + glutarate

-

-

3.5.1.93

4 entries

Substrate in Enzyme-catalyzed Reactions (18 results)

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Show Substrate (18 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

3.1.1.1

7-amino cephalosporanic acid + H2O = ?

681338

-

3.1.1.1

7-aminocephalosporanic acid + H2O = (6R,7R)-7-amino-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid + acetate

749674

-

3.1.1.1

2 entries

3.1.1.2

7-aminocephalosporanic acid + H2O = ?

750166

-

3.1.1.41

7-amino-cephalosporanic acid + H2O = 7-amino-3-deacetylcephalosporanic acid + acetate

749261

-

3.1.1.41

7-aminocephalosporanic acid + H2O = 7-amino-3-deacetylcephalosporanic acid + acetate

749261, 677538

-

3.1.1.41

7-aminocephalosporanic acid + H2O = acetate + deacetyl-7-aminocephalosporanic acid

170664, 170666, 170667, 170673, 170677, 170672, 170668, 649397, 747164, 749261

-

3.1.1.41

7-aminocephalosporanic acid + H2O = deacetyl 7-aminocephalosporanic acid + acetate

746975, 671502

-

3.1.1.43

D-alpha-phenylglycine methyl ester + 7-aminocephalosporanic acid = methanol + ?

80934, 80936

-

3.1.1.43

glycine ethyl ester + 7-aminocephalosporanic acid = ethanol + ?

80936

-

3.1.1.6

7-aminocephalosporanic acid + H2O = ?

730907

-

3.1.1.6

7-aminocephalosporanic acid + H2O = deacetylated 7-aminocephalosporanic acid + acetate

663817

-

3.1.1.72

7-amino cephalosporanic acid + H2O = ? + acetate

751984

-

3.1.1.72

7-aminocephalosporanic acid + H2O = ?

677538

-

3.1.1.72

7-aminocephalosporanic acid = acetate + ?

23606

-

3.5.1.11

7-aminocephalosporanic acid + (R)-mandelic acid = 7-[(1-hydroxy-1-phenyl)-acetamido]-3-acetoxymethyl-D3-cephem-4-carboxylic acid

668443

-

3.5.1.11

7-aminocephalosporanic acid + D-alpha-phenylglycine methylester = ?

680992

-

3.5.2.6

(6R,7R)-3-[(acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate + H2O = (2R)-5-[(acetyloxy)methyl]-2-[(R)-amino(carboxy)methyl]-3,6-dihydro-2H-1,3-thiazine-4-carboxylate

711378

-

3.5.2.6

7beta-aminocephalosporanic acid + H2O = (2R)-5-[(acetyloxy)methyl]-2-[(R)-amino(carboxy)methyl]-3,6-dihydro-2H-1,3-thiazine-4-carboxylic acid

666141, 696728

-

3.1.1.41

4 entries

3.1.1.43

2 entries

3.1.1.6

2 entries

3.1.1.72

3 entries

3.5.1.11

2 entries

3.5.2.6

2 entries

Product in Enzyme-catalyzed Reactions (32 results)

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Show Product (32 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.4.3.3

cephalosporin C + H2O + O2 = 7-aminocephalosporanic acid + ? + H2O2

-

-

3.1.1.41

alpha-ketoadipinyl-7-aminocephalosporanic acid + H2O = 7-aminocephalosporanic acid + alpha-ketoadipate

-

-

3.1.1.41

deacetyl-7-aminocephalosporanic acid + ethyl acetate = 7-aminocephalosporanic acid + ethanol

170676

-

3.1.1.41

deacetyl-7-aminocephalosporanic acid + ethylene glycol diacetate = 7-aminocephalosporanic acid + ?

170675

-

3.1.1.41

deacetyl-7-aminocephalosporanic acid + isopropenyl acetate = 7-aminocephalosporanic acid + ?

170675

-

3.1.1.41

deacetyl-7-aminocephalosporanic acid + methyl acetate = 7-aminocephalosporanic acid + methanol

170676

-

3.1.1.41

glutaryl-7-aminocephalosporanic acid + H2O = 7-aminocephalosporanic acid + glutamate

-

-

3.5.1.11

cephalothin + H2O = thiophen-2-ylacetic acid + (6R,7R)-3-acetoxymethyl-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

-

-

3.5.1.11

cephalothin + H2O = (6R,7R)-3-[(acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid + (thiophen-2-yl)acetic acid

-

-

3.5.1.11

cephalosporin + H2O = 7-aminocephalosporanic acid + an amino acid

171886,

-

3.5.1.11

cephalosporin C + H2O = 7-aminocephalosporanic acid + (R)-2-aminohexadioic acid

-

-

3.5.1.11

glutaryl-7-aminocephalosporanic acid + H2O = glutarate + 7-aminocephalosporanic acid

-

-

3.1.1.41

6 entries

3.5.1.11

5 entries

3.5.1.14

cephalosporin C + H2O = 7-aminocephalosporanic acid + ?

-

-

3.5.1.93

(7R)-7-(4-carboxybutanamido)cephalosporanate + H2O = (7R)-7-aminocephalosporanate + glutarate

-

-

3.5.1.93

cephalosporin C + H2O = (7R)-7-aminocephalosporanate + 2-aminoadipate

-

-

3.5.1.93

adipyl-7-aminocephalosporanic acid + H2O = 7-aminocephalosporanate + adipate

-

-

3.5.1.93

adipyl-7-aminocephalosporanic acid + H2O = adipate + 7-aminocephalosporanate

-

-

3.5.1.93

cephalosporin C + H2O = 7-aminocephalosporanate + 2-amino-5-hydroxypentanoate

-

-

3.5.1.93

glutaryl-7-amino cephalosporanic acid + H2O = 7-aminocephalosporanate + glutarate

-

-

3.5.1.93

glutaryl-7-aminocephalosporanic acid + H2O = 7-aminocephalosporanate + glutarate

-

-

3.5.1.93

glutaryl-7-aminocephalosporanic acid + H2O = glutarate + 7-aminocephalosporanate

-

-

3.5.1.93

pentanoyl-7-aminocephalosporanic acid + H2O = pentanoate + 7-aminocephalosporanate

-

-

3.5.1.93

succinyl-7-aminocephalosporanic acid + H2O = 7-aminocephalosporanate + succinate

-

-

3.5.1.93

succinyl-7-aminocephalosporanic acid + H2O = succinate + 7-aminocephalosporanate

-

-

3.5.1.93

7beta-(4-carboxylbutanamino)cephalosporanic acid + H2O = 7-aminocephalosporanic acid + pentanoate

-

-

3.5.1.93

adipyl-7-aminocephalosporanic acid + H2O = 7-aminocephalosporanic acid + adipate

-

-

3.5.1.93

cephalosporin C + H2O = 7-aminocephalosporanic acid + 2-amino-5-hydroxypentanoate

-

-

3.5.1.93

cephalosporin C + H2O = 7-aminocephalosporanic acid + ?

-

-

3.5.1.93

D-glutamyl-7-aminocephalosporanic acid + H2O = 7-aminocephalosporanic acid + D-glutamate

-

-

3.5.1.93

D-glutamyl-7-aminocephalosporanic acid + H2O = 7-aminocephalosporanic acid + glutamate

-

-

3.5.1.93

glutaryl-7-aminocephalosporanic acid + H2O = 7-aminocephalosporanic acid + glutarate

-

-

3.5.1.93

succinyl-7-aminocephalosporanic acid + H2O = 7-aminocephalosporanic acid + succinate

-

-

3.5.1.93

19 entries

Inhibitor in Enzyme-catalyzed Reactions (5 results)

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Show Inhibitors (5 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

3.4.11.19

-

647080

-

3.5.1.93

product inhibition

733836

-

3.5.1.93

20 mM, 81% inhibition

661368

-

3.5.1.93

competitive

662549

-

3.5.1.93

product inhibition, competitive inhibitor

713590

-

3.5.1.93

4 entries

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (13 results)

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Show Turnover Number (13 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

3.1.1.1

11.8

-

pH 7.0, 25°C

681338

3.1.1.1

46.7

-

recombinant mutant NaM1H2, pH 8.5, 30°C

749674

3.1.1.1

133.3

-

recombinant wild-type enzyme, pH 8.5, 30°C

749674

3.1.1.2

61.3

-

free enzyme, at pH 8.0 and 30°C

750166

3.1.1.2

69.5

-

immobilized cross-linked enzyme aggregate, at pH 8.0 and 30°C

750166

3.1.1.41

15.5

-

mutant lacking 10 amino acids at N-terminus, pH 8.0, 50°C

749261

3.1.1.41

20.2

-

mutant lacking 4 amino acids at N-terminus, pH 8.0, 50°C

749261

3.1.1.41

23.8

-

wild-type, pH 8.0, 50°C

749261

3.1.1.41

24.8

-

wild-type including expression and purification tag, pH 8.0, 50°C

749261

3.1.1.41

576

-

-

170672

3.5.1.93

0.0485

-

pH and temperature not specified in the publication

711538

3.5.1.93

0.508

-

D445G mutant, pH and temperature not specified in the publication

711538

3.1.1.1

3 entries

3.1.1.2

2 entries

3.1.1.41

5 entries

3.5.1.93

2 entries

3.5.2.6

0.46

-

pH and temperature not specified in the publication

711378

K_M Value (19 results)

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Show KM Value (19 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

3.1.1.1

0.46

-

recombinant wild-type enzyme, pH 8.5, 30°C

749674

3.1.1.1

0.51

-

recombinant mutant NaM1H2, pH 8.5, 30°C

749674

3.1.1.1

3.02

-

pH 7.0, 25°C

681338

3.1.1.2

74.6

-

immobilized cross-linked enzyme aggregate, at pH 8.0 and 30°C

750166

3.1.1.2

98.7

-

free enzyme, at pH 8.0 and 30°C

750166

3.1.1.41

1.12

-

mutant lacking 4 amino acids at N-terminus, pH 8.0, 50°C

749261

3.1.1.41

1.135

-

wild-type, pH 8.0, 50°C

749261

3.1.1.41

1.384

-

wild-type including expression and purification tag, pH 8.0, 50°C

749261

3.1.1.41

1.43

-

-

170672

3.1.1.41

1.563

-

mutant lacking 10 amino acids at N-terminus, pH 8.0, 50°C

749261

3.1.1.41

2.8

-

-

170664, 170666, 170667

3.1.1.41

6.5

-

strain ATCC6633

170673

3.1.1.41

7.4

-

recombinant enzyme, 30°C

170677

3.1.1.41

7.9

-

strain SHS 0133, FERM BP-2755

170673

3.1.1.41

8.3

-

pH 8, 37°C

649397

3.1.1.41

20.8

-

pH 7.3, 25°C

747164

3.1.1.1

3 entries

3.1.1.2

2 entries

3.1.1.41

11 entries

3.5.1.93

-999

-

estimated value: 9.43 mg/ml, pH 7.6, 34°C, Vmax: 7.65 U/ml

711051

3.5.2.6

0.29

-

pH and temperature not specified in the publication

711378

3.5.2.6

0.29

-

pH 7.5, 25°C

696728

3.5.2.6

2 entries

K_i Value (5 results)

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Show KI Value (5 entries)

EC NUMBER

KI VALUE [MM]

KI VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

3.5.1.93

1

-

recombinant mutant H57betaS/H70betaS/I176betaT, pH 8.0, 25°C

733836

3.5.1.93

1.4

-

-

662549

3.5.1.93

2

-

recombinant mutant H57betaS/H70betaS/R24betaP, pH 8.0, 25°C

733836

3.5.1.93

2

-

-

662549

3.5.1.93

2.3

-

-

662549

3.5.1.93

5 entries

References & Links

Literature References (37)

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Show Reference (37 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

23606

9286998

Isolation, analysis, and expression of two genes from Thermoanaerobacterium sp. strain JW/SL YS485: a beta-xylosidase and a novel acetyl xylan esterase with cephalosporin C deacetylase activity

1997

Lorenz, W.W.; Wiegel, J.

J. Bacteriol.

179

5436-5441

80934

-

Substrate specificity of alpha-amino acid hydrolase from Xanthomonas citri

1980

Kato, K.; Kawahara, K.; Takahashi, T.; Kakinuma, A.

Agric. Biol. Chem.

44

1075-1081

80936

4424889

Substrate specificity of an alpha-amino acid ester hydrolase produced by Acetobacter turbidans A.T.C.C. 9325

1974

Takahashi, T.; Yamazaki, Y.; Kato, K.

Biochem. J.

137

497-503

170664

953166

Immobilization of a cephalosporin acetylesterase by containment within an ultrafiltration device

1976

Abbott, B.J.; Cerimele, B.; Fukuda, D.S.

Biotechnol. Bioeng.

18

1033-1042

170666

241292

Physical properties and kinetic behavior of a cephalosporin acetylesterase produced by Bacillus subtilis

1975

Abbott, B.J.; Fukuda, D.S.

Appl. Microbiol.

30

413-419

170667

237223

Cephalosporin acetylesterase (Bacillus subtilis)

1978

Abbott, B.J.; Fukuda, D.S.

Methods Enzymol.

43

731-734

170668

237222

Cephalosporin acetylesterase (citrus)

1975

Abraham, E.P.; Fawcett, P.

Methods Enzymol.

43

728-731

170672

-

Purification and properties of cephalosporin-C deacetylase from the yeast, Rhodotorula glutinis 38B1, useful for bioconversion of 7-aminocephalosporanic acid derivatives

1998

Sakai, Y.; Abe, T.; Aoki, M.; Ohabayashi, Y.; Yamamoto, K.; Tani, Y.; Kato, N.

J. Ferment. Bioeng.

85

53-57

170673

-

Purification, characterization and partial amino acid sequences of a novel cephalosporin-C deacetylase from Bacillus subtilis

1994

Takimoto, A.; Mitsushima, K.; Yagi, S.; Sonoyama, T.

J. Ferment. Bioeng.

77

17-22

170675

9406399

Purification and characterization of a cephalosporin esterase from Phodosporidium toruloides

1997

Politino, M.; Tonzi, S.M.; Burnett, W.V.; Romancik, G.; Usher, J.J.

Appl. Environ. Microbiol.

63

4807-4811

170676

16535370

Bioconversion of 7-aminocephalosporanic acid by intact Rhodotorula glutinis cells

1996

Sakai, Y.; Abe, T.; Ohbayashi, Y.; Isaka, K.; Yamamoto, K.; Tani, Y.; Kato, N.

Appl. Environ. Microbiol.

62

2669-2672

170677

16232499

High-level expression, purification, and some properties of a recombinant cephalosporin-C deacetylase

1999

Takimoto, A.; Yagi, S.; Mitsushima, K.

J. Biosci. Bioeng.

87

456-462

171886

805897

Penicillin acylase (assay)

1975

Cole, M.; Savidge, T.; vander Haeghe, H.

Methods Enzymol.

43

698-705

647080

1540587

Structural similarity of D-aminopeptidase to carboxypeptidase DD and beta-lactamases

1992

Asano, Y.; Kato, Y.; Yamada, A.; Kondo, K.

Biochemistry

31

2316-2328

649397

11030579

A cephalosporin C acetylhydrolase is present in the cultures of Nocardia lactamdurans

2000

Cardoza, R.E.; Velasco, J.; Martin, J.F.; Liras, P.

Appl. Microbiol. Biotechnol.

54

406-412

661368

9756463

An acidic glutaryl-7-aminocephalosporanic acid acylase from Pseudomonas nitroreducens

1998

Lee, Y.H.; Chang, T.S.; Liu, H.J.; Chu, W.S.

Biotechnol. Appl. Biochem.

28

113-118

662549

-

Comparative characterization of new glutaryl 7-ACA and cephalosporin C acylases

1992

Aramori, I.; Fukagawa, M.; Tsumura, M.; Iwami, M.; Ono, H.; Ishitani, Y.; Koji, H.; Kohsaka, M.; Ueda, Y.; Imanaka, H.

J. Ferment. Bioeng.

73

185-192

663817

-

Acetyl esterase from Mediterranean oranges: Partial purification, immobilization and biotransformations

2004

Pasta, P.; Verga, R.; Zambianchi, F.; Daminati, M.

Biocatal. Biotransform.

22

221-224

666141

16776502

Synthesis and evaluation of ketophosph(on)ates as beta-lactamase inhibitors

2006

Perumal, S.K.; Pratt, R.F.

J. Org. Chem.

71

4778-4785

668443

-

Penicillin G acylase catalyzed acylation of 7-ACA in aqueous two-phase systems using kinetically and thermodynamically controlled strategies: improved enzymatic synthesis of 7-[(1-hydroxy-1-phenyl)-acetamido]-3-acetoxymethyl-D3-cephem-4-carboxylic acid

2005

Terreni, M.; Ubiali, D.; Pagani, G.; Hernandez-Justiz, O.; Fernandez-Lafuente, R.; Guisan, J.M.

Enzyme Microb. Technol.

36

672-679

671502

15069587

Batch production of deacetyl 7-aminocephalosporanic acid by immobilized cephalosporin-C deacetylase

2004

Takimoto, A.; Takakura, T.; Tani, H.; Yagi, S.; Mitsushima, K.

Appl. Microbiol. Biotechnol.

65

263-267

677538

17651681

A colorimetric assay for the determination of acetyl xylan esterase or cephalosporin C acetyl esterase activities using 7-amino cephalosporanic acid, cephalosporin C, or acetylated xylan as substrate

2007

Martinez-Martinez, I.; Montoro-Garcia, S.; Lozada-Ramirez, J.D.; Sanchez-Ferrer, A.; Garcia-Carmona, F.

Anal. Biochem.

369

210-217

680992

1367491

Expression of penicillin G acylase gene from Bacillus megaterium ATCC 14945 in Escherichia coli and Bacillus subtilis

1991

Kang, J.H.; Hwang, Y.; Yoo, O.J.

J. Biotechnol.

17

99-108

681338

-

Expression and characterization of a new esterase cloned directly from Agrobacterium tumefaciens genome

2006

Park, H.; Kim, Y.; Kim, H.

J. Microbiol. Biotechnol.

16

145-148

696728

18572409

beta -Ketophosphonates as beta -lactamase inhibitors: Intramolecular cooperativity between the hydrophobic subsites of a class D beta -lactamase

2008

Perumal, S.K.; Adediran, S.A.; Pratt, R.F.

Bioorg. Med. Chem.

16

6987-6994

711051

20677902

Biosynthesis of cephalosporin-C acylase enzyme: optimal media design, purification, and characterization

2010

Gaurav, K.; Kundu, K.; Kundu, S.

Artif. Cells Blood Substit. Immobil. Biotechnol.

38

277-283

711378

19243936

Approaches to the simultaneous inactivation of metallo- and serine-beta-lactamases

2009

Ganta, S.R.; Perumal, S.; Pagadala, S.R.; Samuelsen, O.; Spencer, J.; Pratt, R.F.; Buynak, J.D.

Bioorg. Med. Chem. Lett.

19

1618-1622

711538

20572278

Enhancement of glutaryl-7-aminocephalosporanic acid acylase activity of gamma-glutamyltranspeptidase of Bacillus subtilis

2010

Suzuki, H.; Yamada, C.; Kijima, K.; Ishihara, S.; Wada, K.; Fukuyama, K.; Kumagai, H.

Biotechnol. J.

5

829-837

713590

100054187

Characteristic of immobilized cephalosporin C acylase and its application in one-step enzymatic conversion of cephalosporin C to 7-aminocephalosporanic acid

2011

Zhu, X.; Luo, H.; Chang, Y.; Su, H.; Li, Q.; Yu, H.; Shen, Z.

World J. Microbiol. Biotechnol.

27

823-829

730907

22411095

Functional and structural characterization of a thermostable acetyl esterase from Thermotoga maritima

2012

Levisson, M.; Han, G.W.; Deller, M.C.; Xu, Q.; Biely, P.; Hendriks, S.; Ten Eyck, L.F.; Flensburg, C.; Roversi, P.; Miller, M.D.; McMullan, D.; von Delft, F.; Kreusch, A.; Deacon, A.M.; van der Oost, J.; Lesley, S.A.; Elsliger, M.A.; Kengen, S.W.; Wilson, I.A.

Proteins

80

1545-1559

733836

24684708

Strategic manipulation of an industrial biocatalyst - evolution of a cephalosporin C acylase

2014

Conti, G.; Pollegioni, L.; Molla, G.; Rosini, E.

FEBS J.

281

2443-2455

746975

27181355

Crystal structure of Thermotoga maritima acetyl esterase complex with a substrate analog Insights into the distinctive substrate specificity in the CE7 carbohydrate esterase family

2016

Singh, M.; Manoj, N.

Biochem. Biophys. Res. Commun.

476

63-68

747164

22659119

The structural basis for the narrow substrate specificity of an acetyl esterase from Thermotoga maritima

2012

Hedge, M.; Gehring, A.; Adkins, C.; Weston, L.; Lavis, L.; Johnson, R.

Biochim. Biophys. Acta

1824

1024-1030

749261

28097692

Structural role of a conserved active site cis proline in the Thermotoga maritima acetyl esterase from the carbohydrate esterase family 7

2017

Singh, M.; Manoj, N.

Proteins

85

694-708

749674

29453256

Structural characterization and directed evolution of a novel acetyl xylan esterase reveals thermostability determinants of the carbohydrate esterase 7 family

2018

Adesioye, F.A.; Makhalanyane, T.P.; Vikram, S.; Sewell, B.T.; Schubert, W.D.; Cowan, D.A.

Appl. Environ. Microbiol.

84

e02695-17

750166

26443058

Characterization of cross-linked immobilized arylesterase from Gluconobacter oxydans 621H with activity toward cephalosporin C and 7-aminocephalosporanic acid

2016

Inmaculada, N.; Francisco, G.

Biotechnol. Prog.

32

36-42

751984

30379876

Crystal structure and functional characterization of a cold-active acetyl xylan esterase (PbAcE) from psychrophilic soil microbe Paenibacillus sp.

2018

Park, S.; Yoo, W.; Lee, C.; Jeong, C.; Shin, S.; Kim, H.; Park, H.; Kim, K.; Kim, T.; Lee, J.

PLoS ONE

13

e0206260

Links to other databases for 7-aminocephalosporanic acid

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Show Links (1 entry)

ChEBI

PubChem