Synonym
Viridinomycin; Viridomycin; Antibiotic T-24146; Viridenomycin
IUPAC/Chemical Name
(4E,6E,8E,10Z,16Z,18Z,20E,22E,24R,25S,26R)-25,27-dihydroxy-26-methoxy-4,24-dimethyl-13-phenyl-3-oxa-14-azabicyclo[22.3.0]heptacosa-1(27),4,6,8,10,16,18,20,22-nonaene-2,15-dione
InChi Key
GWYPHKYSRIAIBU-KGZNJIQESA-N
InChi Code
InChI=1S/C34H37NO6/c1-25-19-13-8-4-5-9-16-22-27(26-20-14-12-15-21-26)35-28(36)23-17-10-6-7-11-18-24-34(2)29(33(39)41-25)30(37)31(40-3)32(34)38/h4-21,23-24,27,31-32,37-38H,22H2,1-3H3,(H,35,36)/b5-4+,10-6-,11-7+,13-8+,16-9-,23-17-,24-18+,25-19+/t27?,31-,32+,34+/m0/s1
SMILES Code
O=C(O/C(C)=C/C=C/C=C/C=C\CC(C1=CC=CC=C1)N2)C3=C(O)[C@H](OC)[C@@H](O)[C@]3(C)/C=C/C=C/C=C\C=C/C2=O
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
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
555.67
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: Batsanov AS, Knowles JP, Lightfoot AP, Maw G, Thirsk CE, Twiddle SJ, Whiting A. A novel, efficient, diastereo- and enantioselective Mukaiyama aldol-based synthesis of a vinyl cyclopentanone core derivative of viridenomycin. Org Lett. 2007 Dec 20;9(26):5565-8. Epub 2007 Nov 17. PubMed PMID: 18020354.
2: Hasegawa T, Kamiya T, Henmi T, Iwasaki H, Yamatodani S. Viridenomycin, a new antibiotic. J Antibiot (Tokyo). 1975 Mar;28(3):167-75. PubMed PMID: 1079209.
3: Knowles JP, O'Connor VE, Whiting A. Studies towards the synthesis of the northern polyene of viridenomycin and synthesis of Z-double bond analogues. Org Biomol Chem. 2011 Mar 21;9(6):1876-86. doi: 10.1039/c0ob00977f. Epub 2011 Jan 31. PubMed PMID: 21283899.
4: Batsanov AS, Knowles JP, Whiting A. Mechanistic studies on the Heck-Mizoroki cross-coupling reaction of a hindered vinylboronate ester as a key approach to developing a highly stereoselective synthesis of a C1-C7 Z,Z,E-triene synthon for viridenomycin. J Org Chem. 2007 Mar 30;72(7):2525-32. Epub 2007 Mar 3. PubMed PMID: 17335239.
5: Nakagawa M, Toda Y, Furihata K, Hayakawa Y, Seto H. Studies on viridenomycin, a novel 24-membered macrocyclic polyene lactam antibiotic. J Antibiot (Tokyo). 1992 Jul;45(7):1133-8. PubMed PMID: 1517159.
6: Trost BM, Jiang C. Pd-catalyzed asymmetric allylic alkylation. A short route to the cyclopentyl core of viridenomycin. Org Lett. 2003 May 1;5(9):1563-5. PubMed PMID: 12713324.
