WS1279
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Bioactive by-products |
| Catalog number | BBF-01640 |
| CAS | 129712-27-2 |
| Molecular Weight | 1312.8 |
| Molecular Formula | C68H125N7O15S |
Online Inquiry
Description
WS1279 is a lipopeptide isolated from the fermentation broth of Streptomyces willmorei No. 1279. It stimulated the proliferation of mouse bone marrow cells in vitro and accelerated the recovery of granulocyte counts in bone marrow from leukopenia induced by mitomycin C (MMC) in mice.
Specification
| Synonyms | WS 1279; WS-1279; S-(2,3-bis(palmitoyloxy)propyl)-N-palmitoyl-L-cysteinyl-L-asparaginyl-L-serylglycylglycyl-L-serine |
| IUPAC Name | (2S)-2-[[2-[[2-[[(2S)-2-[[(2S)-4-amino-2-[[(2R)-3-[2,3-di(hexadecanoyloxy)propylsulfanyl]-2-(hexadecanoylamino)propanoyl]amino]-4-oxobutanoyl]amino]-3-hydroxypropanoyl]amino]acetyl]amino]acetyl]amino]-3-hydroxypropanoic acid |
| Canonical SMILES | CCCCCCCCCCCCCCCC(=O)NC(CSCC(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NC(CC(=O)N)C(=O)NC(CO)C(=O)NCC(=O)NCC(=O)NC(CO)C(=O)O |
| InChI | InChI=1S/C68H125N7O15S/c1-4-7-10-13-16-19-22-25-28-31-34-37-40-43-60(79)73-58(67(86)74-55(46-59(69)78)66(85)75-56(49-76)65(84)71-47-61(80)70-48-62(81)72-57(50-77)68(87)88)53-91-52-54(90-64(83)45-42-39-36-33-30-27-24-21-18-15-12-9-6-3)51-89-63(82)44-41-38-35-32-29-26-23-20-17-14-11-8-5-2/h54-58,76-77H,4-53H2,1-3H3,(H2,69,78)(H,70,80)(H,71,84)(H,72,81)(H,73,79)(H,74,86)(H,75,85)(H,87,88)/t54?,55-,56-,57-,58-/m0/s1 |
| InChI Key | MKKXXGNBLGERJB-JBZFGHNVSA-N |
Properties
| Appearance | White Powder |
Reference Reading
1. Synthesis and mitogenic activity of chiral lipopeptide WS1279 and its derivatives
M Kurimura, A Ochiai, K Achiwa Chem Pharm Bull (Tokyo). 1993 Nov;41(11):1965-70. doi: 10.1248/cpb.41.1965.
Optically active lipopeptide derivatives have been synthesized by the use of chiral glycerol derivatives. Lipopeptide WS1279 derivatives with (R)-glycerol moieties showed a higher mitogenic activity than those with the (S)-configuration. Various N-protected lipopeptide and N-deprotected derivatives showed increased mitogenic activity.
2. Structure and synthesis of an immunoactive lipopeptide, WS1279, of microbial origin
Y Tsuda, Y Okada, M Tanaka, N Shigematsu, Y Hori, T Goto, M Hashimoto Chem Pharm Bull (Tokyo). 1991 Mar;39(3):607-11. doi: 10.1248/cpb.39.607.
The structure of WS1279, isolated from Streptomyces sp. as an immunoactive lipopeptide, has been deduced on the basis of chemical and physical evidence as S-[2,3-bis(palmitoyloxy)propyl]-N alpha-palmitoyl-Cys-Asn-Ser-Gly-Gly-Ser- OH. This was confirmed by synthesis.
3. WS1279, a novel lipopeptide isolated from Streptomyces willmorei. Biological activities
M Tanaka, Y Hori, F Sakai, H Ueda, T Goto, M Okuhara, Y Tsuda, Y Okada J Antibiot (Tokyo). 1993 Nov;46(11):1699-706. doi: 10.7164/antibiotics.46.1699.
WS1279, a new lipopeptide isolated from the fermentation broth of Streptomyces willmorei No. 1279, stimulated the proliferation of mouse bone marrow cells in vitro and accelerated the recovery of granulocyte counts in bone marrow from leukopenia induced by mitomycin C (MMC) in mice. The glycerylcysteine moiety of WS1279 is necessary and the lipid peptide structure is required for manifestation of full stimulating activity in vitro. WS1279 was the most effective on the proliferation of bone marrow cells among the tested immunostimulants in vitro. However, the effect of WS1279 on restoration of reduced granulocyte counts in MMC-induced leukopenia in mice was less than that of FK-565, lipopolysaccharide, picibanil or forphenicinol. WS1279 augmented host resistance to infection with Staphylococcus aureus 47 in normal and immunosuppressed mice.
Recommended Products
| BBF-03881 | Sancycline | Inquiry |
| BBF-04727 | Strigolactone GR24 | Inquiry |
| BBF-03827 | Polymyxin B sulphate | Inquiry |
| BBF-01851 | Fumagillin | Inquiry |
| BBF-00693 | Ansamitocin P-3 | Inquiry |
| BBF-04621 | Artemisinin | Inquiry |
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 ╳
