Leustroducsin B | CAS#145142-82-1 | CSF inducer

MedKoo Cat#: 598701 | Name: Leustroducsin B

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Leustroducsin B is a novel colony-stimulating factor (CSF) inducer isolated from Streptomyces platensis SANK 60191.

Chemical Structure

Leustroducsin B

CAS#145142-82-1

Theoretical Analysis

MedKoo Cat#: 598701

Name: Leustroducsin B

CAS#: 145142-82-1

Chemical Formula: C34H56NO10P

Exact Mass: 669.3642

Molecular Weight: 669.79

Elemental Analysis: C, 60.97; H, 8.43; N, 2.09; O, 23.89; P, 4.62

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

No Data

Synonym

Leustroducsin B; LSN B;

IUPAC/Chemical Name

3-((1E,3E,9E)-8-(2-aminoethyl)-10-(3-ethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-5,8-dihydroxy-7-(phosphonooxy)deca-1,3,9-trien-1-yl)cyclohexyl 6-methyloctanoate

InChi Key

ZYSAHMPRXHPPAK-JKWCDDFISA-N

InChi Code

InChI=1S/C34H56NO10P/c1-4-25(3)11-6-9-16-32(37)43-29-15-10-13-26(23-29)12-7-8-14-28(36)24-31(45-46(40,41)42)34(39,21-22-35)20-19-30-27(5-2)17-18-33(38)44-30/h7-8,12,14,17-20,25-31,36,39H,4-6,9-11,13,15-16,21-24,35H2,1-3H3,(H2,40,41,42)/b12-7+,14-8+,20-19+

SMILES Code

CCC(C)CCCCC(OC1CC(/C=C/C=C/C(O)CC(OP(O)(O)=O)C(O)(CCN)/C=C/C2C(CC)C=CC(O2)=O)CCC1)=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.03.00

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 669.79 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Trost BM, Biannic B, Brindle CS, O'Keefe BM, Hunter TJ, Ngai MY. A Highly Convergent Total Synthesis of Leustroducsin B. J Am Chem Soc. 2015 Sep 16;137(36):11594-7. doi: 10.1021/jacs.5b07438. Epub 2015 Sep 1. PubMed PMID: 26313159; PubMed Central PMCID: PMC4621997. 2: Greszler SN, Malinowski JT, Johnson JS. Formal synthesis of leustroducsin B via Reformatsky/Claisen condensation of silyl glyoxylates. Org Lett. 2011 Jun 17;13(12):3206-9. doi: 10.1021/ol2011192. Epub 2011 May 17. PubMed PMID: 21591684; PubMed Central PMCID: PMC3115596. 3: Miyashita K, Tsunemi T, Hosokawa T, Ikejiri M, Imanishi T. Total synthesis of leustroducsin B. J Org Chem. 2008 Jul 18;73(14):5360-70. doi: 10.1021/jo8005599. Epub 2008 Jun 13. PubMed PMID: 18549287. 4: Koishi R, Yoshimura C, Kohama T, Serizawa N. Leustroducsin B activates nuclear factor-kappaB via the acidic sphingomyelinase pathway in human bone marrow-derived stromal cell line KM-102. J Interferon Cytokine Res. 2002 Mar;22(3):343-50. PubMed PMID: 12034042. 5: Shimada K, Kaburagi Y, Fukuyama T. Total synthesis of leustroducsin B. J Am Chem Soc. 2003 Apr 9;125(14):4048-9. PubMed PMID: 12670216. 6: Kohama T, Katayama T, Inukai M, Maeda H, Shiraishi A. Augmentation of host resistance against bacterial infection by treatment with leustroducsin B, a new CSF inducer. Microbiol Immunol. 1994;38(9):741-5. PubMed PMID: 7854215. 7: Koishi R, Serizawa N, Kohama T. The effect of leustroducsin B on the production of cytokines by human mesenchymal cells. J Interferon Cytokine Res. 1998 Oct;18(10):863-9. PubMed PMID: 9809622. 8: Kohama T, Maeda H, Sakai JI, Shiraishi A, Yamashita K. Leustroduscin B, a new cytokine inducer derived from an actinomycetes, induces thrombocytosis in mice. J Antibiot (Tokyo). 1996 Jan;49(1):91-4. PubMed PMID: 8609094. 9: Greszler SN, Malinowski JT, Johnson JS. Remote stereoinduction in the acylation of fully substituted enolates: tandem Reformatsky/quaternary Claisen condensations of silyl glyoxylates and β-lactones. J Am Chem Soc. 2010 Dec 15;132(49):17393-5. doi: 10.1021/ja108848d. Epub 2010 Nov 18. PubMed PMID: 21087044; PubMed Central PMCID: PMC3056164. 10: Kohama T, Nakamura T, Kinoshita T, Kaneko I, Shiraishi A. Novel microbial metabolites of the phoslactomycins family induce production of colony-stimulating factors by bone marrow stromal cells. II. Isolation, physico-chemical properties and structure determination. J Antibiot (Tokyo). 1993 Oct;46(10):1512-9. PubMed PMID: 7503976. 11: Kohama T, Enokita R, Okazaki T, Miyaoka H, Torikata A, Inukai M, Kaneko I, Kagasaki T, Sakaida Y, Satoh A, et al. Novel microbial metabolites of the phoslactomycins family induce production of colony-stimulating factors by bone marrow stromal cells. I. Taxonomy, fermentation and biological properties. J Antibiot (Tokyo). 1993 Oct;46(10):1503-11. PubMed PMID: 7503975.