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

Base Information

• Chemical Name: 6-[(5-Amino-5-carboxypentanoyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• CAS No.: 525-94-0
• Molecular Formula: C14H21 N3 O6 S
• Molecular Weight: 359.403
• NSC Number: 113137
• DSSTox Substance ID: DTXSID30862118
• Wikidata: Q110079885
• Mol file: 525-94-0.mol

Synonyms:NSC113137;SYNNEMATIN B;525-94-0;Adicillinum;Penicillin N;Adicillin;4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(5-amino-5-carboxyvaleramido)-3,3-dimethyl-7-oxo-, D-;4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,6-[[(5R)-5-amino-5-carboxy-1-oxopentyl]amino]-3,3-dimethyl-7-oxo-,(2S,5R,6R)-;(D-4-Amino-4-carboxybutyl) penicillinic acid;6-[(5-amino-5-carboxypentanoyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;SCHEMBL10718068;DTXSID30862118;NCI60_000296;6-(5-Amino-5-carboxypentanamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

Chemical Property of 6-[(5-Amino-5-carboxypentanoyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

Chemical Property:

• Vapor Pressure: 6.59E-24mmHg at 25°C
• Boiling Point: 739.2°Cat760mmHg
• Flash Point: 400.9°C
• PSA: 175.33000
• Density: 1.5g/cm³
• LogP: 0.22940
• XLogP3: -2.5
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 7
• Exact Mass: 359.11510657
• Heavy Atom Count: 24
• Complexity: 581

Purity/Quality:

99%, ^*data from raw suppliers

PENICILLIN N 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C(N2C(S1)C(C2=O)NC(=O)CCCC(C(=O)O)N)C(=O)O)C

Technology Process of 6-[(5-Amino-5-carboxypentanoyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

There total 5 articles about 6-[(5-Amino-5-carboxypentanoyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

(L-α-amino-δ-adipyl)-L-cysteinyl-D-valine (21566-74-5,93133-50-7,141116-68-9,32467-88-2) → isopenicillin N (525-94-0,93864-65-4,58678-43-6)

Guidance literature:

for 1h; incubation with cell-free system from Cephalosporium acremonium C-91;

DOI:10.1021/ja00415a041

Reference yield:

<(5R)-5-amino-5-carboxypentanoyl>-L-cysteinyl-D-valine trifluoroacetate → penicillin N (525-94-0)

Guidance literature:

In water; at 27 ℃; isopenicillin N synthase, dithreitol, L-ascorbate, Fe(SO₄)2, catalase, pH 7.8;

DOI:10.1016/S0040-4020(01)80725-0

Reference yield:

6-Aminopenicillanic Acid (551-16-6) → penicillin N (525-94-0)

Guidance literature:

ueber mehrere Stufen;

upstream raw materials:

δ-(D-α-aminoadipoyl)-L-cysteinyl-D-valine

6-Aminopenicillanic Acid

(L-α-amino-δ-adipyl)-L-cysteinyl-D-valine

Downstream raw materials:

succinic acid

deacethoxycephalosporin C

(2R,3S,6R,7R)-1-aza-3-methyl-3-hydroxy-7-<(5R)-5-amino-5-carboxypentanamido>-8-oxo-5-thiazbicyclo<4.2.0>octane-2-carboxylate

desacetyl cephalosporin C

Refernces

• 1、 Bahadur, Gulam,Baldwin, Jack E.,Field, Leslie D.,Lehtonen, Eeva-M. M.,Usher, John J.,et al.. "Direct 1H N.M.R. Observation of the Cell-free Conversion of δ-(L-α-Aminoadipyl)-L-cysteinyl-D-valine and δ-(L-α-Aminoadipyl)-L-cysteinyl-D-(-)-isoleucine into Penicillins". . p. 917 - 919. Retrieved 1981.
• 2、 Bahadur,Baldwin,Usher,et al.. "Cell-free biosynthesis of penicillins. Conversion of peptides into new beta-lactam antibiotics". . p. 7650 - 7651. Retrieved 1981.
• 3、 Clifton, Ian J.,Ge, Wei,Adlington, Robert M.,Baldwin, Jack E.,Rutledge, Peter J.. "The crystal structure of isopenicillin N synthase with δ-(l-α- aminoadipoyl)-l-cysteinyl-d-methionine reveals thioether coordination to iron". scheme or table. p. 103 - 107. Retrieved 2012/05/20.
• 4、 Baldwin, Jack E.,Adlington, Robert M.,Crouch, Nicholas P.,Pereira, Ines A.C.. "The enzymatic synthesis of isotopically labelled penicillin Ns with isopenicillin N synthase". . p. 1145 - 1163. Retrieved 2007/10/03.