Mycelianamide

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Mycelianamide
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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