ホスホロチオエート
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出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2012/08/17 15:32:20」(JST)
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- For the thiophosphate esters see organothiophosphates.
A thiophosphate (or phosphorothioate) is a family of compounds and anions with the general chemical formula PS4-xOx3- (x = 0, 1, 2, or 3). The state of protonation is usually not specified. They could be bound to as many as three protons for the neutral H3PS4-xOx species. Two protons correspond to the related monoanions, and one proton for the dianions. The trianions are highly basic and do not exist in appreciable concentrations in solution. Thiophosphates are tetrahedral anions, with the phosphorus at the center of the tetrahedron.
Contents
- 1 Monothiophosphate
- 2 Dithiophosphates
- 3 Tri- and tetrathiophosphates
- 4 References
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Monothiophosphate
Ball-and-stick model of the monothiophosphate ion
Monothiophosphates are formally derived from the anion PO3S3-, which has C3v symmetry.. A number of insecticides feature organic monothiophosphate center, including diazinon, parathion, and malathion. They have the formula (RO)2PS(OAr), where R = methyl or ethyl and Ar = an aryl or related group. Coordination complexes of are known.[1]
In the laboratory monothiophosphate is used as an analogue of phosphate in biochemistry. Monothiophosphate esters are biochemical reagents used in the study transcription,[2] substitution interference assays.
Dithiophosphates
Dithiophosphates are formally derived from the anion PO2S23-, which has C2v symmetry. This species is the major product from the reaction of base (e.g., NaOH) with phosphorus pentasulfide. The sodium salt has the nominal formula Na3PO2S2, but is invariably hydrated. The main application of this dithiophosphate salt is in the purification of molybdenite ore. Organic thiophosphates feature the (RO)2PS2- anion (R = alkyl, aryl). Zinc dithiophosphate, e.g., Zn(S2P(OR)2)2, are used as oil additives (R = alkyl).
Tri- and tetrathiophosphates
Trithiophosphates are formally derived from the anion POS33-, which has C3v symmetry. Tetrathiophosphate has the formula PS43-. Derivatives of these two anions are less commonly encountered.
References
- ^ Poat JC et al. (1990). "A thiophosphate bridged platinum–zinc hetero-bimetallic complex: [(Me2PhP)2Pt{OSP(OR)2}2ZnCl2". J. Chem. Soc., Chem. Commun.: 1036–1038. http://www.rsc.org/publishing/journals/article.asp?doi=C39900001036.
- ^ Lorsch JR, Bartel DP, Szostak JW. (1995). "Reverse transcriptase reads through a 2'–5' linkage and a 2'-thiphosphate in a template". Nucleic Acids Res. 23 (15): 2811–2814. doi:10.1093/nar/23.15.2811. PMC 307115. PMID 7544885. http://nar.oxfordjournals.org/cgi/content/abstract/23/15/2811.
Organophosphorus
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Only P-O bonds |
P(III)
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Phosphite/Organophosphite
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P(V)
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Phosphate/Organophosphate
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With P-C bonds |
One P-C bonds
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P(III)
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Phosphonite
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P(V)
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Phosphonate
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Two P-C bonds
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P(III)
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Phosphinite
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P(V)
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Phosphinate
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Three P-C bonds
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P(III)
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Phosphine
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P(V)
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Phosphine oxide
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With P-N bonds |
One P-N bond
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P(III)
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Phosphoramidite (e.g. Nucleoside phosphoramidite)
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P(V)
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Phosphoramidate (e.g. Phosphocreatine)
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Two P-N bond
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P(III)
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Phosphorodiamidite
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P(V)
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Phosphorodiamidate (e.g. Morpholino, Cyclophosphamide)
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Three P-N bond
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P(V)
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Phosphoramide (e.g. Hexamethylphosphoramide, Metepa)
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With P-C and P-N bonds |
One P-C bond and one P-N bond
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One P-C bond and two P-N bond
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Two P-C bond and one P-N bond
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With P-S bonds |
One P-S bond
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P(III)
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Phosphorothioite
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P(V)
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Phosphorothioate
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Two P-S bond
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P(III)
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Phosphorodithioite
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P(V)
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Phosphorodithioate
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UpToDate Contents
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English Journal
- Cleavable Molecular Beacon for Hg(2+) Detection Based on Phosphorothioate RNA Modifications.
- Huang PJ1, Wang F1, Liu J1.
- Analytical chemistry.Anal Chem.2015 Jul 7;87(13):6890-5. doi: 10.1021/acs.analchem.5b01362. Epub 2015 Jun 23.
- Mercury is a highly toxic heavy metal, and detection of Hg(2+) by biosensors has attracted extensive research interest in the past decade. In particular, a number of DNA-based sensing strategies have been developed. Well-known examples include thymine-Hg(2+) interactions and Hg(2+)-activated DNAzyme
- PMID 26060876
- DNA-Encoded Tuning of Geometric and Plasmonic Properties of Nanoparticles Growing from Gold Nanorod Seeds.
- Song T1,2, Tang L2,3, Tan LH2, Wang X1, Satyavolu NS2, Xing H2, Wang Z2, Li J3, Liang H4, Lu Y5.
- Angewandte Chemie (International ed. in English).Angew Chem Int Ed Engl.2015 Jul 6;54(28):8114-8. doi: 10.1002/anie.201500838. Epub 2015 Jun 10.
- Systematically controlling the morphology of nanoparticles, especially those growing from gold nanorod (AuNR) seeds, are underexplored; however, the AuNR and its related morphologies have shown promises in many applications. Herein we report the use of programmable DNA sequences to control AuNR over
- PMID 26096755
- Expression profile analysis of silkworm P450 family genes after phoxim induction.
- Li F1, Ni M1, Zhang H1, Wang B1, Xu K1, Tian J1, Hu J1, Shen W2, Li B3.
- Pesticide biochemistry and physiology.Pestic Biochem Physiol.2015 Jul;122:103-9. doi: 10.1016/j.pestbp.2014.12.013. Epub 2014 Dec 17.
- Silkworm (Bombyx mori) is an important economic insect and a model species for Lepidopteran. Each year, O,O-diethyl O-(alpha-cyanobenzylideneamino) phosphorothioate (phoxim) pesticide poisoning in China results in huge economic losses in sericulture. Silkworm fat body is the main organ for nutrient
- PMID 26071814
Japanese Journal
- 田之畑 大二郎,真田 雄介,望月 慎一,宮本 寛子,櫻井 和朗
- 高分子論文集 advpub(0), 2015
- 筆者らは,β-1,3-グルカンの1種であるシゾフィラン(SPG)が核酸と複合体を形成すること,その複合体が核酸医薬の薬物送達システム(Drug delivery system:DDS)の材料として利用できることを見いだした.DDSとしての有効性の検証はもちろんのことながら,その開発の基礎となり,かつ,薬事申請で必要となる複合体の構造や水溶液中での性質など基礎物性を明らかにすることは極めて重要な課題 …
- NAID 130004793196
- 田之畑 大二郎,真田 雄介,望月 慎一 [他],宮本 寛子,櫻井 和朗
- 高分子論文集 72(2), 37-47, 2015
- 筆者らは,β-1,3-グルカンの1種であるシゾフィラン(SPG)が核酸と複合体を形成すること,その複合体が核酸医薬の薬物送達システム(Drug delivery system:DDS)の材料として利用できることを見いだした.DDSとしての有効性の検証はもちろんのことながら,その開発の基礎となり,かつ,薬事申請で必要となる複合体の構造や水溶液中での性質など基礎物性を明らかにすることは極めて重要な課題 …
- NAID 130004793176
- The systemic administration of an anti-miRNA oligonucleotide encapsulated pH-sensitive liposome results in reduced level of hepatic microRNA-122 in mice
- Hatakeyama H,Murata M,Sato Y,Takahashi M,Minakawa N,Matsuda A,Harashima H
- Journal of controlled release 173, 43-50, 2014-01-10
- … Anti-microRNA oligonucleotides including 2'-OMe and phosphorothioate modifications against miR-122 (AMO122) were encapsulated in the YSK05-MEND. …
- NAID 120005597470
Related Links
- S化(Phosphorothioate)の受託サービスをご紹介 ... アンチセンス実験の代表的オリゴ 標的遺伝子の発現のみを特異的に抑制するアンチセンス実験に、 「ホスホロチオエート(S化)オリゴ」が最もよく用いられます。
- Figure 1: Examples of phosphodiester and phosphorothioate internucleotide linkages. back to top Phosphorothioates (or S-oligos) are a variant of normal DNA (See Figure 1) in which one of the nonbridging oxygens is replaced by a ...
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