WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 584808
CAS#: 103913-16-2
Description: Oxetanocin A is an antiviral that comes from Bacillus megaterium NK84-0218.
MedKoo Cat#: 584808
Name: Oxetanocin A
CAS#: 103913-16-2
Chemical Formula: C10H13N5O3
Exact Mass: 251.1018
Molecular Weight: 251.246
Elemental Analysis: C, 47.81; H, 5.22; N, 27.88; O, 19.10
This product is not in stock, which may be available by custom synthesis.
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Synonym: Oxetanocin A; NK 84-0218; Oxetanocin
IUPAC/Chemical Name: 2,3-Oxetanedimethanol, 4-(6-amino-9H-purin-9-yl)-, (2S-(2-alpha,3-beta,4-alpha))-
InChi Key: LMJVXGOFWKVXAW-OXOINMOOSA-N
InChi Code: InChI=1S/C10H13N5O3/c11-8-7-9(13-3-12-8)15(4-14-7)10-5(1-16)6(2-17)18-10/h3-6,10,16-17H,1-2H2,(H2,11,12,13)/t5-,6-,10-/m1/s1
SMILES Code: OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C23)[C@@H]1CO
Appearance: Solid powder
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
The following data is based on the product molecular weight 251.246 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: Rustullet A, Alibés R, de March P, Figueredo M, Font J. Stereoselective route to oxetanocin carbocyclic analogues based on a [2 + 2] photocycloaddition to a chiral 2(5H)-furanone. Org Lett. 2007 Jul 19;9(15):2827-30. Epub 2007 Jun 21. PubMed PMID: 17583347.
2: Bridwell-Rabb J, Zhong A, Sun HG, Drennan CL, Liu HW. A B(12)-dependent radical SAM enzyme involved in oxetanocin A biosynthesis. Nature. 2017 Apr 20;544(7650):322-326. doi: 10.1038/nature21689. Epub 2017 Mar 27. PubMed PMID: 28346939; PubMed Central PMCID: PMC5398914.
3: Sakakibara N, Igarashi J, Takata M, Demizu Y, Misawa T, Kurihara M, Konishi R, Kato Y, Maruyama T, Tsukamoto I. Synthesis and Evaluation of Novel Carbocyclic Oxetanocin A (COA-Cl) Derivatives as Potential Tube Formation Agents. Chem Pharm Bull (Tokyo). 2015;63(9):701-9. doi: 10.1248/cpb.c15-00386. PubMed PMID: 26329863.
4: Bridwell-Rabb J, Kang G, Zhong A, Liu HW, Drennan CL. An HD domain phosphohydrolase active site tailored for oxetanocin-A biosynthesis. Proc Natl Acad Sci U S A. 2016 Nov 29;113(48):13750-13755. Epub 2016 Nov 14. PubMed PMID: 27849620; PubMed Central PMCID: PMC5137760.
5: Maruyama T, Sato Y, Horii T, Shiota H, Nitta K, Shirasaka T, Mitsuya H, Honjo M. Synthesis and antiviral activities of carbocyclic oxetanocin analogues. Chem Pharm Bull (Tokyo). 1990 Oct;38(10):2719-25. PubMed PMID: 1963811.
6: Saijo M, Suzutani T, Yoshida I. Effects of acyclovir, oxetanocin-G, and carbocyclic oxetanocin-G in combinations on the replications of herpes simplex virus type 1 and type 2 in Vero cells. Tohoku J Exp Med. 1992 May;167(1):57-68. PubMed PMID: 1333651.
7: Tseng CK, Marquez VE, Milne GW, Wysocki RJ Jr, Mitsuya H, Shirasaki T, Driscoll JS. A ring-enlarged oxetanocin A analogue as an inhibitor of HIV infectivity. J Med Chem. 1991 Jan;34(1):343-9. PubMed PMID: 1992135.
8: Seki J, Shimada N, Takahashi K, Takita T, Takeuchi T, Hoshino H. Inhibition of infectivity of human immunodeficiency virus by a novel nucleoside, oxetanocin, and related compounds. Antimicrob Agents Chemother. 1989 May;33(5):773-5. PubMed PMID: 2787618; PubMed Central PMCID: PMC172532.
9: Sakakibara N, Igarashi J, Takata M, Konishi R, Kato Y, Tsukamoto I. Synthesis and Evaluation of Novel Cyclopropane Nucleoside as Potential Tube Formation Agents. Chem Pharm Bull (Tokyo). 2017;65(5):504-510. doi: 10.1248/cpb.c17-00056. PubMed PMID: 28458372.
10: Liang Y, Hnatiuk N, Rowley JM, Whiting BT, Coates GW, Rablen PR, Morton M, Howell AR. Access to oxetane-containing psico-nucleosides from 2-methyleneoxetanes: a role for neighboring group participation? J Org Chem. 2011 Dec 16;76(24):9962-74. doi: 10.1021/jo201565h. Epub 2011 Nov 15. PubMed PMID: 22029375.
11: Hayashi S, Norbeck DW, Rosenbrook W, Fine RL, Matsukura M, Plattner JJ, Broder S, Mitsuya H. Cyclobut-A and cyclobut-G, carbocyclic oxetanocin analogs that inhibit the replication of human immunodeficiency virus in T cells and monocytes and macrophages in vitro. Antimicrob Agents Chemother. 1990 Feb;34(2):287-94. PubMed PMID: 2327778; PubMed Central PMCID: PMC171575.
12: Shiota H, Nitta K, Naito T, Mimura Y, Maruyama T. Clinical evaluation of carbocyclic oxetanocin G eyedrops in the treatment of herpes simplex corneal ulcers. Br J Ophthalmol. 1996 May;80(5):413-5. PubMed PMID: 8695561; PubMed Central PMCID: PMC505491.
13: Izuta S, Shimada N, Kitagawa M, Suzuki M, Kojima K, Yoshida S. Inhibitory effects of triphosphate derivatives of oxetanocin G and related compounds on eukaryotic and viral DNA polymerases and human immunodeficiency virus reverse transcriptase. J Biochem. 1992 Jul;112(1):81-7. PubMed PMID: 1385392.
14: Morita M, Tomita K, Ishizawa M, Takagi K, Kawamura F, Takahashi H, Morino T. Cloning of oxetanocin A biosynthetic and resistance genes that reside on a plasmid of Bacillus megaterium strain NK84-0128. Biosci Biotechnol Biochem. 1999 Mar;63(3):563-6. PubMed PMID: 10227144.
15: Masuda A, Kitagawa M, Tanaka A, Saito S, Shimada N, Ikeda R, Hoshino H, Daikoku T, Nishiyama Y. Synthesis and antiviral activity of adenosine deaminase-resistant oxetanocin A derivatives: 2-halogeno-oxetanocin A. J Antibiot (Tokyo). 1993 Jun;46(6):1034-7. PubMed PMID: 8344866.
16: Nagahata T, Kitagawa M, Matsubara K. Effect of oxetanocin G, a novel nucleoside analog, on DNA synthesis by hepatitis B virus virions. Antimicrob Agents Chemother. 1994 Apr;38(4):707-12. PubMed PMID: 7518217; PubMed Central PMCID: PMC284529.
17: De Clercq E. HIV inhibitors targeted at the reverse transcriptase. AIDS Res Hum Retroviruses. 1992 Feb;8(2):119-34. Review. PubMed PMID: 1371690.
18: Sato Y, Maruyama T. Synthesis and antiviral activity of 3'-fluorocarbocyclic oxetanocin A. Chem Pharm Bull (Tokyo). 1995 Jan;43(1):91-5. PubMed PMID: 7895312.
19: Sakakibara N. [Synthesis and evaluation of novel nucleic acid derivatives as bioactive substances]. Yakugaku Zasshi. 2014;134(9):965-72. Review. Japanese. PubMed PMID: 25174367.
20: Nishiyama Y, Yamamoto N, Yamada Y, Fujioka H, Shimada N, Takahashi K. Efficacy of oxetanocin G against herpes simplex virus type 2 and murine cytomegalovirus infections in mice. J Antibiot (Tokyo). 1989 Aug;42(8):1308-11. PubMed PMID: 2547744.
