Mycelianamide
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-01967 |
| CAS | 22775-52-6 |
| Molecular Weight | 400.47 |
| Molecular Formula | C22H28N2O5 |
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Description
Mycelianamide is an antibiotic produced by Pen. griseofulvum. Activity against gram-positive bacteria.
Specification
| Storage | Store at -20°C |
| IUPAC Name | (3E,6S)-3-[[4-[(2E)-3,7-dimethylocta-2,6-dienoxy]phenyl]methylidene]-1,4-dihydroxy-6-methylpiperazine-2,5-dione |
| Canonical SMILES | CC1C(=O)N(C(=CC2=CC=C(C=C2)OCC=C(C)CCC=C(C)C)C(=O)N1O)O |
| InChI | InChI=1S/C22H28N2O5/c1-15(2)6-5-7-16(3)12-13-29-19-10-8-18(9-11-19)14-20-22(26)23(27)17(4)21(25)24(20)28/h6,8-12,14,17,27-28H,5,7,13H2,1-4H3/b16-12+,20-14+/t17-/m0/s1 |
| InChI Key | JIGPABZIAJWQNM-MSODBRDKSA-N |
Properties
| Appearance | White Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Boiling Point | 613.9°C at 760 mmHg |
| Melting Point | 170-172°C (dec.) |
| Density | 1.24 g/cm3 |
| Solubility | Soluble in Methanol, Chloroform, Dioxane, pyridine |
Reference Reading
1. Biosynthesis of gliotoxin and mycelianamide
J C Macdonald, G P Slater Can J Biochem. 1975 Apr;53(4):475-8. doi: 10.1139/o75-066.
Mycelium of Penicillium terlikowski was permeable to both L-[carboxyl-14C]phenylalanine and cyclo L-[carbonyl-14C]phenylalanyl-L-seryl. The former compound was incorporated well and the latter poorly into gliotoxin produced by stationary cultures of the organism. Mycelium of Penicillium patulum was permeablt to L-[CARBONYL-14C]tyrosyl and cyclo L-alanyl-d-[carbonyl-14C]tyrosyl. These cyclic depeptides were not incorporated into mycelianamide produced by stationary cultures of the organism, but both1carboxyl-14C]tyrosine were incorporated. The latter was incorporated in a specific manner into part of the mycelianamide molecule. The results did not support the postulate that the appropriate cyclic dipeptides, as outlined above, were free intermediates in the biosynthesis of gliotoxin or mycelianamide.
2. A butyrylcholinesterase inhibitor produced by Penicillium sp. no. C-81 and its identity with mycelianamide
T Nagasawa, N Mori, Y Tani, K Ogata J Antibiot (Tokyo). 1976 May;29(5):526-31. doi: 10.7164/antibiotics.29.526.
A screening aimed at obtaining a cholinesterase inhibitor of microbial origin was carried out using Pseudomonas butyrylcholinesterase. A mycelium-extract of a fungus strain, belonging to the genus Penicillium, was found to produce such an enzyme inhibitor. The inhibitor was purified and crystallized as colorless leaflets. From physical and chemical studies, the inhibitor was identified as being identical with an antibiotic, mycelianamide, though this compound was not known to have enzyme inhibitor activity. The kinetics of the inhibition of Pseudomonas butyrylcholinesterase were also studied. Horse serum cholinesterase and hog liver carboxylesterase were also inhibited by the isolated Penicillium C-81 inhibitor, but lipase and acetylcholinesterase were not.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
