Sch-37137
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| Category | Antibiotics |
| Catalog number | BBF-03538 |
| CAS | 113737-67-0 |
| Molecular Weight | 288.26 |
| Molecular Formula | C10H16N4O6 |
| Purity | 95% |
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Description
Sch-37137 is a dipeptide antibiotic produced by Micromonospora sp. SCC 1792. It was weakly active against species of Candida and dermatophytes (mean MICs greater than or equal to 128 mg/ml) in Sabouraud dextrose, yeast-nitrogen and modified Eagles minimum essential media; however activity against Candida sp. (mean MICs greater than or equal to 12 mg/ml) and dermatophytes (mean MICs greater than or equal to 0.8 mg/ml) significantly improved in MA medium.
Specification
| Synonyms | Sch 37137; N-L-Alanyl-3-(((3-(aminocarbonyl)oxiranyl)carbonyl)amino)-L-alanine |
| IUPAC Name | [(2S)-2-aminopropanoyl] (2S)-2-amino-3-[[(2R,3R)-3-carbamoyloxirane-2-carbonyl]amino]propanoate |
| Canonical SMILES | CC(C(=O)OC(=O)C(CNC(=O)C1C(O1)C(=O)N)N)N |
| InChI | InChI=1S/C10H16N4O6/c1-3(11)9(17)20-10(18)4(12)2-14-8(16)6-5(19-6)7(13)15/h3-6H,2,11-12H2,1H3,(H2,13,15)(H,14,16)/t3-,4-,5+,6+/m0/s1 |
| InChI Key | ZJOXNGKKGAAFJU-UNTFVMJOSA-N |
Properties
| Appearance | White Amorphous Solid |
| Antibiotic Activity Spectrum | fungi |
| Boiling Point | 636.5ºC at 760mmHg |
| Melting Point | 198°C (dec.) |
| Density | 1.485g/cm3 |
Reference Reading
1. Isolation of CB-25-I, an antifungal antibiotic, from Serratia plymuthica
J Shoji, T Hattori, K Tawara, T Kato, Y Terui, K Matsumoto, H Hinoo, R Sakazaki, J Kikuchi J Antibiot (Tokyo) . 1989 Jun;42(6):869-74. doi: 10.7164/antibiotics.42.869.
A new antifungal antibiotic, CB-25-I, was isolated from the culture broth of a strain of Serratia plymuthica. The antibiotic, a water-soluble dipeptide, is structurally related to Sch 37137 and A 19009, both produced by strains of Actinomycetales. The antibiotic exhibits inhibitory activity against Candida albicans in YNB medium (a synthetic medium), but the activity is significantly reduced in Sabouroud dextrose medium.
2. Synthesis and anticandidal activities of optimized analogs of antibiotic Sch 37137
L Kasprzak, E Borowski, H Chmara, T Zieniawa, R Andruszkiewicz J Antibiot (Tokyo) . 1994 Jun;47(6):715-23. doi: 10.7164/antibiotics.47.715.
Peptide analogues of Sch 37137 the antifungal antibiotic have been synthesized and evaluated in vitro against Candida sp. Di- and tripeptides containing methionine, leucine, norvaline, lysine, glutamic acid and N3-(trans-epoxysuccinamoyl)-L-2,3-diaminopropanoic acid, (EADP) were obtained. Peptides containing (D)-, and (L)-trans-epoxysuccinamic acid were also prepared. All of the analogues examined displayed in general higher anticandidal activity than a mixture of diastereomers of Sch 37137.
3. Amide and ester derivatives of N3-trans-epoxysuccinoyl-L-2,3-diaminopropanoic acid: inhibitors of glucosamine-6-phosphate synthase
E Borowski, R Andruszkiewicz, S Milewski J Enzyme Inhib . 1995;9(2):123-33. doi: 10.3109/14756369509042812.
Several analogs 5, 6, 7, 8, 10 and 11 of the C-terminal fragment of a peptide antibiotic Sch 37137 were designed and tested as inhibitors of glucosamine-6-phosphate synthase from Saccharomyces cerevisiae. From IC50 values and kinetic parameters of inhibition of glucosamine-6-phosphate synthase by compounds 5-11 it has been found that the inhibitory potency of these compounds follows the order: 6 > 5 > 8 > 9 > 7, 10, 11. This suggests that an inhibitor with a primary amido group binds better to the active site of the enzyme than other inhibitors. The order of reactivity of compounds 5-11 may be attributed to a steric inability of the inhibitor to fit into the active site of the enzyme and also indicates the importance of the chirality of trans-epoxysuccinic acid on the inhibitory properties of the synthesized compounds.
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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 ╳
