BE-18257A
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| Category | Enzyme inhibitors |
| Catalog number | BBF-03227 |
| CAS | 136553-73-6 |
| Molecular Weight | 598.69 |
| Molecular Formula | C30H42N6O7 |
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Description
BE-18257 A is an endothelin binding inhibitor produced by Streptomyces misakiensis.
Specification
| Synonyms | Cyclo(valyl-leucyl-tryptophyl-glutamyl-alanyl); Cyclo(L-alanyl-D-valyl-L-leucyl-D-tryptophyl-D-alpha-glutamyl) |
| IUPAC Name | (4R)-4-[[(2R)-2-[[(2S)-2-[[(2R)-2-[[(2S)-2-aminopropanoyl]amino]-3-methylbutanoyl]amino]-4-methylpent-4-enoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-5-oxopentanoic acid |
| Canonical SMILES | CC(C)C(C(=O)NC(CC(=C)C)C(=O)NC(CC1=CNC2=CC=CC=C21)C(=O)NC(CCC(=O)O)C=O)NC(=O)C(C)N |
| InChI | InChI=1S/C30H42N6O7/c1-16(2)12-23(35-30(43)26(17(3)4)36-27(40)18(5)31)29(42)34-24(28(41)33-20(15-37)10-11-25(38)39)13-19-14-32-22-9-7-6-8-21(19)22/h6-9,14-15,17-18,20,23-24,26,32H,1,10-13,31H2,2-5H3,(H,33,41)(H,34,42)(H,35,43)(H,36,40)(H,38,39)/t18-,20+,23-,24+,26+/m0/s1 |
| InChI Key | DHIQQDQGWWOERP-SEHYTIIPSA-N |
Properties
| Appearance | White Powder |
| Melting Point | 1062.0±65.0°C at 760 mmHg |
| Density | 1.2±0.1 g/cm3 |
| Solubility | Soluble in DMSO, Methanol |
Reference Reading
1. 3-Dimethylphosphinothioyl-2(3H)-oxazolone (MPTO), a promising new reagent for racemization-free couplings
T Katoh, M Ueki Int J Pept Protein Res. 1993 Sep;42(3):264-9. doi: 10.1111/j.1399-3011.1993.tb00141.x.
3-Dimethylphosphinothioyl-2(3H)-oxazolone (MPTO) was synthesized, and its ability to effect racemization-free couplings and cyclization of a peptide and its C-terminal epimer was examined. MPTO showed good reactivity in aprotic polar solvents such as N,N-dimethylformamide (DMF) and N-methylpyrrolidone. In reactivity MPTO resembles DPPA and dimethylphosphinothioyl azide (MPTA) previously developed by us, but it is much better than these reagents because the side reactions specific to the azide method could be avoided. In coupling of Z-Gly-Val-OH with H-Val-OMe in DMF at 0 degree C, no racemization was observed without use of racemization-suppressing additives. Slight racemization observed at room temperature could be completely suppressed by addition of HOBt but not by HOSu. The utility of MPTO was demonstrated by the synthesis of cyclo-(D-Trp-D-Glu(OBzl)-Ala-D-Val-Leu), an intermediate for an endothelin-binding inhibitor BE 18257A. In a comparative study using DPPA, MPTA and MPTO, no racemization was observed for MPTA or MPTO, while DPPA caused considerable racemization. When MPTO was used in the presence of HOBt rapid cyclization (3 h at RT) occurred to give the optically pure cyclic product.
2. Isolation and structure determination of a new antibacterial peptide pentaminomycin C from Streptomyces cacaoi subsp. cacaoi
Issara Kaweewan, Hikaru Hemmi, Hisayuki Komaki, Shinya Kodani J Antibiot (Tokyo). 2020 Apr;73(4):224-229. doi: 10.1038/s41429-019-0272-y. Epub 2020 Jan 10.
A new antibacterial peptide named pentaminomycin C was isolated from an extract of Streptomyces cacaoi subsp. cacaoi NBRC 12748T, along with a known peptide BE-18257A. Pentaminomycin C was determined to be a cyclic pentapeptide containing an unusual amino acid, Nδ-hydroxyarginine (5-OHArg), by a combination of ESI-MS and NMR analyses. The structure of pentaminomycin C was determined to be cyclo(-L-Leu-D-Val-L-Trp-L-5-OHArg-D-Phe-). Pentaminomycin C exhibited antibacterial activities against Gram-positive bacteria including Micrococcus luteus, Bacillus subtilis, and Staphylococcus aureus. The biosynthetic gene cluster for pentaminomycin C and BE-18257A was identified from the genome sequence data of S. cacaoi subsp. cacaoi.
3. WS-7338, new endothelin receptor antagonists isolated from Streptomyces sp. No. 7338. I. Taxonomy, fermentation, isolation, physico-chemical properties and biological activities
S Miyata, M Hashimoto, Y Masui, M Ezaki, S Takase, M Nishikawa, S Kiyoto, M Okuhara, M Kohsaka J Antibiot (Tokyo). 1992 Jan;45(1):74-82. doi: 10.7164/antibiotics.45.74.
WS-7338 A, B, C and D, novel endothelin receptor antagonists, have been isolated from fermentation broth of Streptomyces sp. No. 7338. These antagonists were purified from the culture mycelium by extraction with acetone, followed by carbon column chromatography and HPLC. Among them, WS-7338 B showed good activity in an endothelin receptor binding assay with an IC50 of 2.7 x 10(-7) M.
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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 ╳
