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A3835

Ascomycin

Name: Ascomycin
Brand: SIGMA

from Streptomyces hygroscopicus var. ascomyceticus, antibiotic, powder

Synonyme(s) :

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

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A propos de cet article

Formule empirique (notation de Hill) :

C₄₃H₆₉NO₁₂

Numéro CAS:

104987-12-4

Poids moléculaire :

792.01

UNSPSC Code:

12352200

PubChem Substance ID:

24890817

NACRES:

NA.77

MDL number:

MFCD06198665

Form:

powder

Quality level:

200

Service technique

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Propriétés

Nom du produit

Ascomycin from Streptomyces hygroscopicus var. ascomyceticus,

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

Description

General description

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.

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.

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.

Other Notes

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

Classe de stockage

11 - Combustible Solids

wgk

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificats d'analyse (COA)

Lot/Batch Number

0000531963

0000505838

0000363291

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Contenu apparenté

Product Information Sheet - A3835

Product Information Sheet

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)

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)

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