Sanglifehrin D
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| Category | Enzyme inhibitors |
| Catalog number | BBF-02866 |
| CAS | |
| Molecular Weight | 1086.40 |
| Molecular Formula | C61H91N5O12 |
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Description
It is a cyclophilin combination produced by the strain of Streptomyces sp. A92-308110. The affinity of Sanglifehrin D to Cyclophilin is similar to Cyclosporin A. The immunosuppressive effect of Sanglifehrin is lower than Cyclosporin A by mixed lymphocyte reaction assay.
Specification
| Synonyms | SFD |
| IUPAC Name | (3S,6S,9R,12S,14R,15S,16S,17E,19E,22S,25S)-22-[(2E,4E,8S,9S)-10-[(2S,3R,6R,9S,11S)-9-ethyl-3,5,11-trimethyl-8-oxo-1-oxa-7-azaspiro[5.5]undec-4-en-2-yl]-9-hydroxy-8-methyldeca-2,4-dien-2-yl]-16-hydroxy-3-[(3-hydroxyphenyl)methyl]-12-methoxy-12,15-dimethyl-6-propan-2-yl-13,23-dioxa-1,4,7,29-tetrazatricyclo[23.3.1.09,14]nonacosa-17,19-diene-2,5,8,24-tetrone |
| Canonical SMILES | CCC1CC(C2(C(=CC(C(O2)CC(C(C)CCC=CC=C(C)C3CC=CC=CC(C(C4C(CCC(O4)(C)OC)C(=O)NC(C(=O)NC(C(=O)N5CCCC(N5)C(=O)O3)CC6=CC(=CC=C6)O)C(C)C)C)O)O)C)C)NC1=O)C |
| InChI | InChI=1S/C61H91N5O12/c1-12-44-32-41(8)61(64-55(44)70)40(7)31-39(6)52(77-61)35-50(69)37(4)21-15-13-16-22-38(5)51-27-18-14-17-26-49(68)42(9)54-46(28-29-60(10,75-11)78-54)56(71)63-53(36(2)3)57(72)62-48(34-43-23-19-24-45(67)33-43)58(73)66-30-20-25-47(65-66)59(74)76-51/h13-14,16-19,22-24,26,31,33,36-37,39,41-42,44,46-54,65,67-69H,12,15,20-21,25,27-30,32,34-35H2,1-11H3,(H,62,72)(H,63,71)(H,64,70)/b16-13+,18-14+,26-17+,38-22+/t37-,39+,41-,42-,44-,46+,47-,48-,49-,50-,51-,52-,53-,54+,60-,61-/m0/s1 |
| InChI Key | RYRBOTOSXJJGLX-YYUPCZRHSA-N |
Properties
| Appearance | White Powder |
| Melting Point | 137-142°C |
| Solubility | Soluble in Methanol |
Reference Reading
1. Sanglifehrins A, B, C and D, novel cyclophilin-binding compounds isolated from Streptomyces sp. A92-308110. I. Taxonomy, fermentation, isolation and biological activity
J J Sanglier, V Quesniaux, T Fehr, H Hofmann, M Mahnke, K Memmert, W Schuler, G Zenke, L Gschwind, C Maurer, W Schilling J Antibiot (Tokyo). 1999 May;52(5):466-73. doi: 10.7164/antibiotics.52.466.
A novel class of macrolides for which the name sanglifehrins is proposed, has been discovered from actinomycete strains based on their high affinity binding for cyclophilin A (CypA), an immunophilin originally identified as a cytosolic protein binding cyclosporin A (CsA). The sanglifehrins were produced by Streptomyces sp. A92-308110. They were isolated and purified by extraction and several chromatographic, activity-guided steps. Sanglifehrins A and B exhibit a 10 to approximately 20 fold higher affinity for CypA than CsA, whereas the affinity of sanglifehrins C and D for CypA is comparable to that of CsA. Sanglifehrins exhibit a lower immunosuppressive activity than CsA when tested in the mixed lymphocyte reaction. Their in vitro activity indicates that they belong to a novel class of immunosuppressants.
2. Sanglifehrins A, B, C and D, novel cyclophilin-binding compounds isolated from Streptomyces sp. A92-308110. II. Structure elucidation, stereochemistry and physico-chemical properties
T Fehr, J Kallen, L Oberer, J J Sanglier, W Schilling J Antibiot (Tokyo). 1999 May;52(5):474-9. doi: 10.7164/antibiotics.52.474.
A novel class of macrolides, the sanglifehrins, was discovered by screening of actinomycete strains with a cyclophilin-binding assay. The chemical structures and absolute stereochemistries of the sanglifehrins A, B, C and D were determined unambiguously by NMR-techniques and by X-ray crystallography of the complex with cyclophilin A. Sanglifehrin A consists of a 22-membered macrocycle containing a tripeptide subunit and features in position 23 a chain of nine carbon atoms bearing a spirocyclic substituent. Sanglifehrins A and B are genuine metabolites whereas sanglifehrins C and D are artefacts.
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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 ╳
