Synonym
Altemicidin; (-)-Altemicidin; (-) Altemicidin;
IUPAC/Chemical Name
(4aR,6S,7R,7aS)-4-carbamoyl-6-hydroxy-2-methyl-7-(2-sulfamoylacetamido)-2,4a,5,6,7,7a-hexahydro-1H-cyclopenta[c]pyridine-7-carboxylic acid
InChi Key
VZRFZUPFQKSXPV-VPFIQFBESA-N
InChi Code
InChI=1S/C13H20N4O7S/c1-17-3-7(11(14)20)6-2-9(18)13(12(21)22,8(6)4-17)16-10(19)5-25(15,23)24/h3,6,8-9,18H,2,4-5H2,1H3,(H2,14,20)(H,16,19)(H,21,22)(H2,15,23,24)/t6-,8+,9-,13+/m0/s1
SMILES Code
NS(CC(N[C@]1(C(O)=O)[C@]2([C@@]([H])(C[C@@H]1O)C(C(N)=O)=CN(C)C2)[H])=O)(=O)=O
Purity
>90% (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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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
376.38
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: Harmange Magnani CS, Maimone TJ. Dearomative Synthetic Entry into the Altemicidin Alkaloids. J Am Chem Soc. 2021 Jun 2;143(21):7935-7939. doi: 10.1021/jacs.1c04147. Epub 2021 May 21. PMID: 34018391.
2: Hayakawa I, Nagayasu A, Sakakura A. Toward the Synthesis of SB-203207: Construction of Four Contiguous Nitrogen-Containing Stereogenic Centers. J Org Chem. 2019 Dec 6;84(23):15614-15623. doi: 10.1021/acs.joc.9b02627. Epub 2019 Nov 20. PMID: 31702152.
3: Hu Z, Awakawa T, Ma Z, Abe I. Aminoacyl sulfonamide assembly in SB-203208 biosynthesis. Nat Commun. 2019 Jan 14;10(1):184. doi: 10.1038/s41467-018-08093-x. PMID: 30643149; PMCID: PMC6331615.
4: Lankapalli AR, Kannabiran K. Interaction of marine Streptomyces compounds with selected cancer drug target proteins by in silico molecular docking studies. Interdiscip Sci. 2013 Mar;5(1):37-44. doi: 10.1007/s12539-013-0146-0. Epub 2013 Apr 19. PMID: 23605638.
5: Kan T, Kawamoto Y, Asakawa T, Furuta T, Fukuyama T. Synthetic studies on altemicidin: stereocontrolled construction of the core framework. Org Lett. 2008 Jan 17;10(2):169-71. doi: 10.1021/ol701940f. Epub 2007 Dec 15. PMID: 18081299.
6: Banwell MG, Crasto CF, Easton CJ, Forrest AK, Karoli T, March DR, Mensah L, Nairn MR, O'Hanlon PJ, Oldham MD, Yue W. Analogues of SB-203207 as inhibitors of tRNA synthetases. Bioorg Med Chem Lett. 2000 Oct 16;10(20):2263-6. doi: 10.1016/s0960-894x(00)00456-x. PMID: 11055334.
7: Houge-Frydrych CS, Gilpin ML, Skett PW, Tyler JW. SB-203207 and SB-203208, two novel isoleucyl tRNA synthetase inhibitors from a Streptomyces sp. II. Structure determination. J Antibiot (Tokyo). 2000 Apr;53(4):364-72. doi: 10.7164/antibiotics.53.364. PMID: 10866218.
8: Mikhaĭlov VV, Kuznetsova TA, Eliakov GB. Bioaktivnye soedineniia morskikh aktinomitsetov [Bioactive compounds from marine actinomycetes]. Bioorg Khim. 1995 Jan;21(1):3-8. Russian. PMID: 7710421.
9: Takahashi A, Ikeda D, Nakamura H, Naganawa H, Kurasawa S, Okami Y, Takeuchi T, IitakaY. Altemicidin, a new acaricidal and antitumor substance. II. Structure determination. J Antibiot (Tokyo). 1989 Nov;42(11):1562-6. doi: 10.7164/antibiotics.42.1562. PMID: 2584138.
10: Takahashi A, Kurasawa S, Ikeda D, Okami Y, Takeuchi T. Altemicidin, a new acaricidal and antitumor substance. I. Taxonomy, fermentation, isolation and physico-chemical and biological properties. J Antibiot (Tokyo). 1989 Nov;42(11):1556-61. doi: 10.7164/antibiotics.42.1556. PMID: 2584137.
