G2201-C

G2201-C

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Category Antibiotics
Catalog number BBF-03576
CAS 66655-93-4
Molecular Weight 142.11
Molecular Formula C6H6O4

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Description

G2201-C is originally isolated from Streptomyces cattleya. It is resistant to Gram-positive bacteria and has a weak anti-Gram-negative activity.

Specification

Synonyms Antibiotic G2201-C; G 2201C; BRN 2083813; 5-hydroxy-5-(hydroxymethyl)cyclopent-2-ene-1,4-dione
IUPAC Name 2-hydroxy-2-(hydroxymethyl)cyclopent-4-ene-1,3-dione
Canonical SMILES C1=CC(=O)C(C1=O)(CO)O
InChI InChI=1S/C6H6O4/c7-3-6(10)4(8)1-2-5(6)9/h1-2,7,10H,3H2
InChI Key ASRUSYCVDJKOBU-UHFFFAOYSA-N

Properties

Appearance Yellow Crystalline
Antibiotic Activity Spectrum Gram-positive bacteria; Gram-negative bacteria
Boiling Point 376.9°C at 760 mmHg
Melting Point 52°C
Density 1.596 g/cm3

Reference Reading

1. Chemical properties and biological activities of cyclopentenediones: a review
Zuzana Sevcíková, Milan Pour, David Novák, Jitka Ulrichová, Jan Vacek Mini Rev Med Chem. 2014 Apr;14(4):322-31. doi: 10.2174/1389557514666140306130207.
Cyclopentenediones (CPDs) are secondary metabolites of higher plants, fungi, algae, cyanobacteria and bacteria. A common denominator of CPDs is the cyclopent-4-ene-1,3-dione skeleton (1), which is modified by several functional groups. The heterogeneity of these substitutions is reflected in around one hundred CPDs reported to date. Most of the derivatives were isolated primarily from plant sources. Synthetic analogues were then prepared with new biological activities and more interesting pharmacological potential. Antifungal substances called coruscanones (2, 3) are the most studied of the CPDs. Other intensely investigated CPDs include lucidone (4), linderone (5), asterredione (6), involutone (7), nostotrebin 6 (8), TX-1123 (9), G2201-C (10), madindolines (11, 12) and many others. In addition to antibacterial and antifungal effects, a broad spectrum of biological activities for CPDs has been reported in the past two decades, especially anti-inflammatory, cytostatic and specific enzyme inhibitory activities. The CPD skeleton has been identified in a number of substances isolated from the plant kingdom; hence, CPDs can be referred to as a new group of natural bioactive substances. The main goal of this review is to define CPDs with respect to basic chemistry, isolation, synthetic approaches and description of their biological effects. Special attention is given to a detailed view into biological activities of CPDs in vitro and their phamacological potential.
2. The application of materials balancing to the characterization of sequential secondary metabolite formation in Streptomyces cattleya NRRL 8057
M E Bushell, A Fryday J Gen Microbiol. 1983 Jun;129(6):1733-41. doi: 10.1099/00221287-129-6-1733.
The high substrate yield factor (0.73 g biomass g glucose-1) and low R.Q. (respiratory quotient, i.e. mol CO2 evolved per mol O2 consumed) value (0.8) measured during growth-phase batch cultures of Streptomyces cattleya could be rationalized in terms of the fermentation mass balance when the oxidized elemental composition of biomass was considered. R.Q. was also indicative of the sequence of secondary metabolite formation, the value rising in steps as each new product was formed. The period of maximum respiratory activity and phosphate uptake preceded maximum growth and glucose uptake. At the end of the lytic phase, a cyclopentenedione cobalt chelator was produced. The termination of lysis coincided with melanin production. Sequential cephamycin C and thienamycin production then took place. Specific hyphal protein content (per unit RNA) peaked before the production of each new metabolite. Melanin, cephamycin C and thienamycin production were initiated when glucose, ammonia and phosphate, respectively, became growth-limiting.
3. G2201-C, a new cyclopentenedione antibiotic, isolated from the fermentation broth of Streptomyces cattleya
M Noble, D Noble, R A Fletton J Antibiot (Tokyo). 1978 Jan;31(1):15-8. doi: 10.7164/antibiotics.31.15.
Streptomyces cattleya produced a new cyclopentenedione antibiotic, G2201-C [C6H6O4(I)], which is moderatley active in vitro against Gram-positive bacteria, weakly active against Gram-negative bacteria, and inactive against fungi. G2201-C is toxic to mice.

Bio Calculators

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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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