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A3835

Sigma-Aldrich

Ascomycin from Streptomyces hygroscopicus var. ascomyceticus

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Synonym(s):
Changchuanmycin, FK-520, FR900520, Immunomycin, L 683590
Empirical Formula (Hill Notation):
C43H69NO12
CAS Number:
104987-12-4
Molecular Weight:
792.01
MDL number:
MFCD06198665
UNSPSC Code:
12352200
PubChem Substance ID:
24890817
NACRES:
NA.77

form

powder

Quality Level

200

greener alternative product score

old score: 59
new score: 54
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greener alternative product characteristics

Designing Safer Chemicals
Design for Energy Efficiency
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

antibiotic activity spectrum

fungi

greener alternative category

, Re-engineered

Mode of action

enzyme | inhibits

storage temp.

−20°C

SMILES string

CCC1\C=C(C)\C[C@H](C)C[C@H](OC)C2O[C@](O)([C@H](C)C[C@@H]2OC)C(=O)C(=O)N3CCCC[C@H]3C(=O)OC([C@H](C)[C@@H](O)CC1=O)\C(C)=C\[C@@H]4CC[C@@H](O)[C@@H](C4)OC

InChI

1S/C43H69NO12/c1-10-30-18-24(2)17-25(3)19-36(53-8)39-37(54-9)21-27(5)43(51,56-39)40(48)41(49)44-16-12-11-13-31(44)42(50)55-38(28(6)33(46)23-34(30)47)26(4)20-29-14-15-32(45)35(22-29)52-7/h18,20,25,27-33,35-39,45-46,51H,10-17,19,21-23H2,1-9H3/b24-18+,26-20+/t25-,27+,28+,29-,30+,31-,32+,33-,35+,36-,37-,38+,39+,43+/m0/s1

InChI key

ZDQSOHOQTUFQEM-NURRSENYSA-N

Related Categories

General description

Ascomycin (FK520) is a macrolide and macrolactone antibiotic isolated from the soil bacterium, Streptomyces hygroscopicus var. ascomyceticus. Ascomycin is a C21 ethyl analog of the macrolide tacrolimus (FK-506). It is a 23-membered polyketide macrolide.
Chemical structure: macrolactam
We are committed to bringing you Greener Alternative Products, which adhere to one of the four categories of Greener Alternatives . This product belongs to category of Re-engineered products, showing key improvements in Green Chemistry Principles “Designing Safer Chemicals” and “Design for Energy Efficiency”. Click here to view its DOZN scorecard.

Biochem/physiol Actions

Ascomycin is a strong immunosuppressant. It inhibits allogenic T-lymphocyte proliferation and can bind with high affinity to FKBP and inhibits calcineurin phosphatase in the nM range.
Ascomycin (FK520) possesses high anti-fungal and immunosuppressant activity. Ascomycin has been shown to inhibit the peptidyl-prolyl cis-trans isomerase activity of FK-506-binding proteins of T cells.

Linkage

An FK506 analog with an ethyl rather than an allyl group at position 21.

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

监管及禁止进口产品

Certificates of Analysis (COA)

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Engineering of the LysR family transcriptional regulator FkbR1 and its target gene to improve ascomycin production
Song K, et al.
Applied Microbiology and Biotechnology, 101(11), 4581-4592 (2017)
Metabolic network model guided engineering ethylmalonyl-CoA pathway to improve ascomycin production in Streptomyces hygroscopicus var. ascomyceticus
Wang J, et al.
Microbial cell factories, 16(1), 1-13 (2017)
Discovery of Less Nephrotoxic FK506 Analogs and Determining Immunophilin Dependence of Immunosuppressant Nephrotoxicity with a Novel Single-Dose Rat Cisplatin Potentiation Assay
Mollison KW, et al.
Journal of Pharmacology and Experimental Therapeutics, 283(3), 1509-1519 (1997)
Comparison of FK-506, rapamycin, ascomycin, and cyclosporine in mouse models of host-versus-graft disease and heterotopic heart transplantation.
K W Mollison et al.
Annals of the New York Academy of Sciences, 685, 55-57 (1993-06-23)
M Kawai et al.
FEBS letters, 316(2), 107-113 (1993-01-25)
The immunosuppressive agent FK-506 has received much attention due to its efficacy and potency in the areas of transplant rejection and autoimmune disease. Calcineurin, a Ca(2+)-calmodulin activated phosphatase, was recently implicated in the immunosuppressive mechanism of FK-506. In our ongoing
View All Related Papers

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