IUPAC/Chemical Name
6,13,20-Trioxa-3,10,17,22,23,24-hexaazatetracyclo(17.2.1.1(5,8).1(12,15))tetracosa-5(24),12(23),19(22)-triene-2,9,16-trione, 7,14,21-trimethyl-4,11,18-tris(1-methylethyl)-, (1S-(1R*,4R*,7S*,8R*,11R*,14S*,15R*,18R*,21S*))-
InChi Key
MIDTUAMKJJDHAR-YAWPOEEYSA-N
InChi Code
InChI=1S/C27H42N6O6/c1-10(2)16-25-31-20(13(7)37-25)23(35)29-18(12(5)6)27-33-21(15(9)39-27)24(36)30-17(11(3)4)26-32-19(14(8)38-26)22(34)28-16/h10-21H,1-9H3,(H,28,34)(H,29,35)(H,30,36)/t13-,14-,15-,16+,17+,18+,19+,20+,21+/m1/s1
SMILES Code
O=C(N[C@@H](C(C)C)C1=N[C@@](C(N[C@@H](C(C)C)C2=N[C@@](C(N[C@H]3C(C)C)=O)([H])[C@@H](C)O2)=O)([H])[C@@H](C)O1)[C@]4([H])[C@@H](C)OC3=N4
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
546.67
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 |
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2: Thiazole and Oxazole Alkaloids: Isolation and Synthesis Danilo Davyt, Gloria Serra Mar Drugs. 2010; 8(11): 2755–2780. Published online 2010 Nov 5. doi: 10.3390/md8112755 PMCID: PMC2996175
3: Bistratamides M and N, Oxazole-Thiazole Containing Cyclic Hexapeptides Isolated from Lissoclinum bistratum Interaction of Zinc (II) with Bistratamide K Carlos Urda, Rogelio Fernández, Jaime Rodríguez, Marta Pérez, Carlos Jiménez, Carmen Cuevas Mar Drugs. 2017 Jul; 15(7): 209. Published online 2017 Jul 1. doi: 10.3390/md15070209 PMCID: PMC5532651
4: Natural Products from Cyanobacteria: Focus on Beneficial Activities Justine Demay, Cécile Bernard, Anita Reinhardt, Benjamin Marie Mar Drugs. 2019 Jun; 17(6): 320. Published online 2019 May 30. doi: 10.3390/md17060320 PMCID: PMC6627551
5: Indole Alkaloids of the Stigonematales (Cyanophyta): Chemical Diversity, Biosynthesis and Biological Activity Katherine Walton, John P. Berry Mar Drugs. 2016 Apr; 14(4): 73. Published online 2016 Apr 6. doi: 10.3390/md14040073 PMCID: PMC4849077
6: Genome mining for natural product biosynthetic gene clusters in the Subsection V cyanobacteria Melinda L. Micallef, Paul M. D’Agostino, Deepti Sharma, Rajesh Viswanathan, Michelle C. Moffitt BMC Genomics. 2015; 16(1): 669. Published online 2015 Sep 3. doi: 10.1186/s12864-015-1855-z PMCID: PMC4558948
7: Naturally Occurring Oxazole-Containing Peptides Jessica T. Mhlongo, Edikarlos Brasil, Beatriz G. de la Torre, Fernando Albericio Mar Drugs. 2020 Apr; 18(4): 203. Published online 2020 Apr 10. doi: 10.3390/md18040203 PMCID: PMC7231064
8: Marine Natural Product Peptides with Therapeutic Potential: Chemistry, Biosynthesis, and Pharmacology Vedanjali Gogineni, Mark T. Hamann Biochim Biophys Acta. Author manuscript; available in PMC 2019 Jan 1.Published in final edited form as: Biochim Biophys Acta. 2018 Jan; 1862(1): 81–196. Published online 2017 Aug 24. doi: 10.1016/j.bbagen.2017.08.014 PMCID: PMC5918664
9: Cyanobactins—ribosomal cyclic peptides produced by cyanobacteria Kaarina Sivonen, Niina Leikoski, David P. Fewer, Jouni Jokela Appl Microbiol Biotechnol. 2010 May; 86(5): 1213–1225. Published online 2010 Feb 27. doi: 10.1007/s00253-010-2482-x PMCID: PMC2854353
10: Fluorocyclisation via I(I)/I(III) catalysis: a concise route to fluorinated oxazolines Felix Scheidt, Christian Thiehoff, Gülay Yilmaz, Stephanie Meyer, Constantin G Daniliuc, Gerald Kehr, Ryan Gilmour Beilstein J Org Chem. 2018; 14: 1021–1027. Published online 2018 May 9. doi: 10.3762/bjoc.14.88 PMCID: PMC6009682