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A3835

Sigma-Aldrich

Ascomycin from Streptomyces hygroscopicus var. ascomyceticus

greener alternative

Synonym(s):

Changchuanmycin, FK-520, FR900520, Immunomycin, L 683590

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About This Item

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
Find out more about DOZN™ Scoring

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

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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_germany

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Rapamycin from Streptomyces hygroscopicus ≥95% (HPLC), powder

Sigma-Aldrich

R0395

Rapamycin from Streptomyces hygroscopicus

Tacrolimus Pharmaceutical Secondary Standard; Certified Reference Material

Supelco

PHR1809

Tacrolimus

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)
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
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)
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)
K Hoogtanders et al.
Journal of pharmaceutical and biomedical analysis, 44(3), 658-664 (2006-12-23)
In a preliminary investigation an assay for tacrolimus based on fingerprick sampling and consecutive application as a blood spot on sampling paper has been developed. The dried blood spot was analysed by HPLC-tandem mass spectrometry. The validated range was 1-30
View All Related Papers

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