5-Deoxy-5-aminoshikimic acid

Base Information

• Chemical Name: 5-Deoxy-5-aminoshikimic acid
• CAS No.: 178948-66-8
• Molecular Formula: C7H11NO4
• Molecular Weight: 173.169
• UNII: 74Z3GVA58B
• DSSTox Substance ID: DTXSID70332123
• Nikkaji Number: J2.054.722G
• Wikipedia: Aminoshikimic_acid
• Wikidata: Q4746471
• Metabolomics Workbench ID: 69809
• Mol file: 178948-66-8.mol

Synonyms:5-amino-5-deoxyshikimic acid;aminoshikimic acid

Chemical Property of 5-Deoxy-5-aminoshikimic acid

Chemical Property:

• PSA: 103.78000
• LogP: -0.84950
• XLogP3: -4.3
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 173.06880783
• Heavy Atom Count: 12
• Complexity: 225

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1C(C(C(C=C1C(=O)O)O)O)N
• Isomeric SMILES: C1[C@H]([C@@H]([C@@H](C=C1C(=O)O)O)O)N

Technology Process of 5-Deoxy-5-aminoshikimic acid

There total 7 articles about 5-Deoxy-5-aminoshikimic 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: 5.0%

D-Glucose (2280-44-6) → shikimic acid (138-59-0) + 5-deoxy-5-amino-shikimic acid (178948-66-8)

Guidance literature:

D-Glucose; With Bacillus pumilus ATCC 21143; oxygen; In various solvent(s); at 30 ℃; for 96h; Microbiological reaction;

Escherichia coli SP_1.1/pJG_6.181B; With oxygen; In various solvent(s); at 37 ℃; Microbiological reaction;

DOI:10.1021/ol049666e

Reference yield: 0.4%

D-Glucose (2280-44-6) → 5-deoxy-5-amino-shikimic acid (178948-66-8) + Rifamycin B (13929-35-6)

Guidance literature:

With oxygen; In various solvent(s); at 28 ℃; for 288h; Microbiological reaction;

DOI:10.1021/ol049666e

Reference yield:

(-)-methyl (1β,2α,6β)-2-hydroxy-7-oxabicyclo<4,1,0>hept-3-ene-4-carboxylate (76985-84-7) → 5-deoxy-5-amino-shikimic acid (178948-66-8)

Guidance literature:

With ammonium hydroxide; for 168h; Ambient temperature;

DOI:10.1021/ja00038a090

upstream raw materials:

(-)-methyl (1β,2α,6β)-2-hydroxy-7-oxabicyclo<4,1,0>hept-3-ene-4-carboxylate

methyl (3R,4S,5R)-5-amino-3,4-dihydroxycyclohex-1-ene-1-carboxylate

D-Glucose

shikimic acid

Downstream raw materials:

5-amino-S₃P

5-deoxy-5-amino-3-dehydroshikimic acid

(3R,4S,5R)-5-amino-3,4-dihydroxy-cyclohex-1-enecarboxylic acid ethyl ester methanesulfonic acid

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