- Glycosidic Bond Cleavage of Thymidine by Low-Energy Electrons
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Thymidine was exposed to low-energy electrons (LEE) as a thin solid film under a high vacuum. Nonvolatile radiation products, remaining on the irradiated surface, were analyzed by HPLC/UV and GC/MS. Here, we show that exposure of thymidine to 3-100 eV electrons gives thymine as a major product with a yield of 3.2 × 10-2 per electron (about one-third of the total decomposition of thymidine). The formation of thymine indicates that LEE induces cleavage of the glycosidic bond separating the base and sugar moieties, suggesting a nonionizing resonant process involving dissociative attachment (a new mechanism of DNA damage involving the interaction of LEE. Copyright
- Zheng, Yi,Cloutier, Pierre,Hunting, Darel J.,Wagner, J. Richard,Sanche, Leon
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- Efficient production of 2-deoxyribose 5-phosphate from glucose and acetaldehyde by coupling of the alcoholic fermentation system of baker's yeast and deoxyriboaldolase-expressing Escherichia coli
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2-Deoxyribose 5-phosphate production through coupling of the alcoholic fermentation system of baker's yeast and deoxyriboaldolase-expressing Escherichia coli was investigated. In this process, baker's yeast generates fructose 1,6-diphosphate from glucose and inorganic phosphate, and then the E. coli convert the fructose 1,6-diphosphate into 2-deoxyribose 5-phosphate via D-glyceraldehyde 3-phosphate. Under the optimized conditions with toluene-treated yeast cells, 356 mM (121 g/l) fructose 1,6-diphosphate was produced from 1,111 mM glucose and 750 mM potassium phosphate buffer (pH 6.4) with a catalytic amount of AMP, and the reaction supernatant containing the fructose 1,6-diphosphate was used directly as substrate for 2-deoxyribose 5-phosphate production with the E. coli cells. With 178 mM enzymatically prepared fructose 1,6-diphosphate and 400 mM acetaldehyde as substrates, 246 mM (52.6 g/l) 2-deoxyribose 5-phosphate was produced. The molar yield of 2-deoxyribose 5-phosphate as to glucose through the total two step reaction was 22.1%. The 2-deoxyribose 5-phosphate produced was converted to 2-deoxyribose with a molar yield of 85% through endogenous or exogenous phosphatase activity.
- Horinouchi, Nobuyuki,Ogawa, Jun,Kawano, Takako,Sakai, Takafumi,Saito, Kyota,Matsumoto, Seiichiro,Sasaki, Mie,Mikami, Yoichi,Shimizu, Sakayu
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- Persistence of N7-(2,3,4-trihydroxybutyl)guanine adducts in the livers of mice and rats exposed to 1,3-butadiene
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Liquid chromatography (LC) in combination with tandem mass spectrometry (MS/MS) and stable isotope methodology was employed for the analysis of the N7-guanine (Gua) adducts derived from 1,2:3,4-diepoxybutane (BDO2) a reactive metabolite of 1,3-butadiene (BD). Two diastereomeric forms of N7- (2,3,4-trihydroxybutyl)guanine (THBG) were identified in the livers of both mice and rats. One of the diastereomers [(±)-THBG] was formed by reaction of DNA with (±)-BDO2, and the other diastereomer (meso-THBG) was formed by reaction of DNA with meso-BDO2. There was significantly more (±)-THBG and meso-THBG in the liver DNA of the mice when compared with those of the rats during the 10 days of exposure to BD and the 6 days of postexposure that were monitored. There was a 2-fold excess of (±)-THBG over meso-THBG in the rat liver at all the time points. In the mouse liver after 10 days of exposure to BD, the (±)-THBG (3.9 adducts/106 normal bases) was also present in an almost 2-fold excess over meso-THBG (2.2 adducts/106 normal bases). However, 6-days after exposure to BD, (±)THBG (1.2 adducts/106 normal bases) and meso-THBG (1.0 adduct/106 normal bases) were present in almost equal amounts in the mouse liver. Furthermore, there was an almost 5-fold excess of the two THBG diastereomers in the mouse liver DNA 6 days after exposure to BD when compared with rat liver DNA. The half-lives of (±)-THBG and meso-THBG appeared to be slightly longer in mouse liver (4.1 and 5.5 days, respectively) than in rat liver (3.6 and 4.0 days, respectively). The apparent persistence of these adducts in the mouse may contribute to the increased susceptibility of this species to BD-induced carcinogenesis. It is possible that (±)-THBG and meso-THBG could have also been derived from the reaction of DNA with the hydrolysis product of BDO2, 1,2-dihydroxy-3,4- epoxybutane (DHEB). Surprisingly, a vast majority of the studies in which the mutagenic and carcinogenic potential of BDO2 have been examined have only employed the commercially available (±)-BDO2. In light of the present findings, additional studies will be required to determine the potency of meso-BDO2 and the DHEB that is the precursor to meso-THBG as mutagens and carcinogens.
- Oe, Tomoyuki,Kambouris, Sara J.,Walker, Vernon E.,Meng, Quanxin,Recio, Leslie,Wherli, Suzanne,Chaudhary, Ajai K.,Blair, Ian A.
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- ACYLOXY TRI(ISOPROPOXY)TITANIUM REAGENTS FOR REGIOSELECTIVE CLEAVAGE OF 2,3-EPOXYALCOHOLS. A SYNTHESIS OF 2-DEOXY-D-RIBOSE.
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The cleavage of the oxirane ring of 3,4-anhydro-2-deoxy-D-threo-pentose diethyl acetal by various acetic acid derivatives - titanium(IV) isopropoxide combinations are reported in detail.The high regioselectivity found with tri(isopropoxy)titanium acetate serves as the basis for a synthesis of 2-deoxy-D-ribose and its ethyl furanosides in high yields and optical purity from non-carbohydrate precursors.The synthesis of other acyloxy tri(isopropoxy)titanium reagents is also described.
- Raifeld, Yuri E.,Nikitenko, Antonia,Arshava, Boris M.
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- Prebiotic phosphorylation of 2-thiouridine provides either nucleotides or DNA building blocks via photoreduction
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Breakthroughs in the study of the origin of life have demonstrated how some of the building blocks essential to biology could have been formed under various primordial scenarios, and could therefore have contributed to the chemical evolution of life. Missing building blocks are then sometimes inferred to be products of primitive biosynthesis, which can stretch the limits of plausibility. Here, we demonstrate the synthesis of 2′-deoxy-2-thiouridine, and subsequently 2′-deoxyadenosine and 2-deoxyribose, under prebiotic conditions. 2′-Deoxy-2-thiouridine is produced by photoreduction of 2,2′-anhydro-2-thiouridine, which is in turn formed by phosphorylation of 2-thiouridine—an intermediate of prebiotic RNA synthesis. 2′-Deoxy-2-thiouridine is an effective deoxyribosylating agent and may have functioned as such in either abiotic or proto-enzyme-catalysed pathways to DNA, as demonstrated by its conversion to 2′-deoxyadenosine by reaction with adenine, and 2-deoxyribose by hydrolysis. An alternative prebiotic phosphorylation of 2-thiouridine leads to the formation of its 5′-phosphate, showing that hypotheses in which 2-thiouridine was a key component of early RNA sequences are within the bounds of synthetic credibility.
- Xu, Jianfeng,Green, Nicholas J.,Gibard, Clémentine,Krishnamurthy, Ramanarayanan,Sutherland, John D.
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p. 457 - 462
(2019/04/08)
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- Enzymatic synthesis of ribo- and 2′-deoxyribonucleosides from glycofuranosyl phosphates: An approach to facilitate isotopic labeling
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Milligram quantities of α-D-ribofuranosyl 1-phosphate (sodium salt) (αR1P) were prepared by the phosphorolysis of inosine, catalyzed by purine nucleoside phosphorylase (PNPase). The αR1P was isolated by chromatography in >95% purity and characterized by 1H and 13C NMR spectroscopy. Aqueous solutions of αR1P were stable at pH 6.4 and 4 °C for several months. The isolated αR1P was N-glycosylated with different nitrogen bases (adenine, guanine and uracil) using PNPase or uridine phosphorylase (UPase) to give the corresponding ribonucleosides in high yield based on the glycosyl phosphate. This methodology is attractive for the preparation of stable isotopically labeled ribo- and 2′-deoxyribonucleosides because of the ease of product purification and convenient use and recycling of nitrogen bases. The approach eliminates the need for separate reactions to prepare individual furanose-labeled ribonucleosides, since only one ribonucleoside (inosine) needs to be labeled, if desired, in the furanose ring, the latter achieved by a high-yield chemical N-glycosylation. 2′-Deoxyribonucleosides were prepared from 2′-deoxyinosine using the same methodology with minor modifications.
- Zhang, Wenhui,Turney, Toby,Surjancev, Ivana,Serianni, Anthony S.
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p. 125 - 133
(2017/08/08)
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- A 2-deoxy-D-ribose preparation method
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The invention discloses a preparation method of 2-deoxidation-D-ribose. The method comprises the following steps: (1) carrying out a Reformasky reaction on D-glyceraldehyde acetonide and ethyl bromoacetate at an inert atmosphere and under a catalytic action of active zinc powder so as to obtain a compound shown in the formula I; (2) carrying out a substitution reaction on the compound shown in the formula I and an organic silicon protecting agent in the presence of an alkali so as to obtain a compound shown in the formula II; (3) carrying out a reduction reaction on the compound shown in the formula II under the condition of a reducing agent so as to obtain a compound shown in the formula III; (4) carrying out an oxidation reaction on the compound shown in the formula III under the condition of an oxidizing agent so as to obtain a compound shown in the formula IV; (5) carrying out deprotection on the compound shown in the formula IV in the presence of an acid and then carrying out a cyclization reaction so as to obtain the 2-deoxidation-D-ribose. According to the method, the Reformasky reaction is adopted, so that the selectivity is good; the high-yield compound shown in the formula I is obtained. The method is convenient to operate, low in raw material cost and easy to industrialize.
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Paragraph 0067; 0076; 0077
(2019/02/02)
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- A new synthetic strategy for 2-deoxy-D-ribose via palladium(II)-catalyzed cyclization of aldehyde
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We achieved a total synthesis of 2-deoxy-D-ribose through intramolecular Pd(II)-catalyzed cyclization of aldehyde via an unstable hemiacetal intermediate as a key step. The Japan Institute of Heterocyclic Chemistry.
- Miyazawa, Masahiro,Awasaguchi, Ken-Ichiro,Uoya, Ikuyo,Yokoyama, Hajime,Hirai, Yoshiro
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p. 1891 - 1902
(2011/04/12)
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- Transition state analysis of thymidine hydrolysis by human thymidine phosphorylase
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Human thymidine phosphorylase (hTP) is responsible for thymidine (dT) homeostasis, and its action promotes angiogenesis. In the absence of phosphate, hTP catalyzes a slow hydrolytic depyrimidination of dT yielding thymine and 2-deoxyribose (dRib). Its transition state was characterized using multiple kinetic isotope effect (KIE) measurements. Isotopically enriched thymidines were synthesized enzymatically from glucose or (deoxy)ribose, and intrinsic KIEs were used to interpret the transition state structure. KIEs from [1′- 14C]-, [1-15N]-, [1′-3H]-, [2′R-3H]-, [2′S-3H]-, [4′- 3H]-, and [5′-3H]dTs provided values of 1.033 ± 0.002, 1.004 ± 0.002, 1.325 ± 0.003, 1.101 ± 0.004, 1.087 ± 0.005, 1.040 ± 0.003, and 1.033 ± 0.003, respectively. Transition state analysis revealed a stepwise mechanism with a 2-deoxyribocation formed early and a higher energetic barrier for nucleophilic attack of a water molecule on the high energy intermediate. An equilibrium exists between the deoxyribocation and reactants prior to the irreversible nucleophilic attack by water. The results establish activation of the thymine leaving group without requirement for phosphate. A transition state constrained to match the intrinsic KIEs was found using density functional theory. An active site histidine (His116) is implicated as the catalytic base for activation of the water nucleophile at the rate-limiting transition state. The distance between the water nucleophile and the anomeric carbon (rC-O) is predicted to be 2.3 A at the transition state. The transition state model predicts that deoxyribose adopts a mild 3′-endo conformation during nucleophilic capture. These results differ from the concerted bimolecular mechanism reported for the arsenolytic reaction (Birck, M. R.; Schramm, V. L. J. Am. Chem. Soc. 2004, 126, 2447-2453).
- Schwartz, Phillip A.,Vetticatt, Mathew J.,Schramm, Vern L.
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supporting information; experimental part
p. 13425 - 13433
(2010/12/19)
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- α,β-Methylene-2′-deoxynucleoside 5′-triphosphates as noncleavable substrates for DNA polymerases: Isolation, characterization, and stability studies of novel 2′-deoxycyclonucleosides, 3,5′-cyclo-dG, and 2,5′-cyclo-dT
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We report synthesis and characterization of a complete set of α,β-methylene-2′-dNTPs (α,β-m-dNTP; N = A, C, T, G, 12-15) in which the α,β-oxygen linkage of natural dNTP was replaced by a methylene group. These nucleotides were designed to be noncleavable substrates for DNA polymerases. Synthesis entails preparation of 2′-deoxynucleoside 5′-diphosphate precursors, followed by an enzymatic γ-phosphorylation. All four synthesized α,β-m-dNTPs were found to be potent inhibitors of polymerase β, with Ki values ranging 1-5 μM. During preparation of the dG and dT derivatives of α,β-methylene diphosphate, we also isolated significant amounts of 3,5′-cyclo-dG (16) and 2,5′-cyclo-dT (17), respectively. These novel 2′-deoxycyclonucleosides were formed via a base-catalyzed intramolecular cyclization (N3 → C5′ and O2 → C5′, respectively). In acidic solution, both 16 and 17 underwent glycolysis, followed by complete depurination. When exposed to alkaline conditions, 16 underwent an oxidative deamination to produce 3,5′-cyclo-2′-deoxyxanthosine (19), whereas 17 was hydrolyzed exclusively to dT.
- Liang, Fengting,Jain, Nidhi,Hutchens, Troy,Shock, David D.,Beard, William A.,Wilson, Samuel H.,Chiarelli, M. Paul,Cho, Bongsup P.
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experimental part
p. 6460 - 6470
(2009/10/23)
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- Azacytosine analogs and derivatives
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Compounds and compositions of azacytosine analogs and derivatives are provided. In one aspect of the invention, analogs or derivatives of decitabine and azacitidine are provided with modification at the 4- and 6-position of the triazine ring, at the 1′-6′position of the ribose ring, or combinations thereof. Methods of synthesizing and manufacturing these analogs and derivatives are also provided. These compounds can be formulated into pharmaceutical compositions that can be used for treating any disease that is sensitive to the treatment with decitabine or azacitidine, such as hematological disorders and cancer.
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Page/Page column 4; sheet 3
(2008/06/13)
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- Synthesis of 7-halogenated 8-aza-7-deaza-2'-deoxyguanosines and related pyrazolo[3,4-d]pyrimidine 2'-deoxyribonucleosides
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The synthesis of 7-bromo and 7-iodo derivatives of 8-aza-7-deaza-2'- deoxyguanosine (2, 3) as well as the halogenated 4-alkoxy derivatives 4a-c and 5a-c is described. Glycosylation of the halogenated pyrazolo[3,4- d]pyrimidine anions of 7a-c or 8a-c with 2-deoxy-3,5-di-O-(p-toluoy)-α-D- erythro-pentofuranosyl chloride (9) yields regioisomeric glycosylation products, the N(1)-isomers 10a-c and 11a-c as well sa the N(2)-compounds 12a- c. The latter isomers lose their halogen during the glycosylation in the presence of non-anhydrous KOH. Anhydrous conditions (NaH) furnished 10c, 11c together with the halogenated N(2)-isomers 13a,b. Compounds 10a-c, and 11a-c were deprotected and converted to the 4-alkoxy nucleosides 4a-c and 5a-c. The N(1)-nucleosides 4c and 5c were hydrolyzed to give the 7-bromo or 7-iodo derivatives of 8-aza-7-deaza-2'-deoxyguanosines 2 and 3. Different from regular 2'-deoxyribonucleosides the sugar moiety of pyrazolo[3,4-d]pyrimidine 2'-deoxyribonucleosides shows a preferred N-type pucker (3T2) in solution, a conformation which is also detected in the solid state.
- Seela, Frank,Becher, Georg
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p. 207 - 214
(2007/10/03)
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- N7-DNA: Synthesis and base pairing of oligonucleotides containing 7-(2-deoxy-β-D-erythro-pentofuranosyl)adenine (N7A(d))
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The synthesis of oligonucleotides containing 7-(2-deoxy-β-D-erythro-pentofuranosyl)adenine (N7A(d); 1) is described. Compound 1 was obtained from the precursor 4-amino-1H-imidazole-5-carbonitrile 2-deoxyribonucleoside 6 and was found to be much more labile than A(d). The N6-benzoyl protecting group (see 8) destabilized the N-glycosylic bond further and was difficult to remove by NH3-catalyzed hydrolysis. Therefore, a (dimethylamino)methylidene residue was introduced (→9). Amidine 9 was blocked at OH-C(5') with the dimethoxytrityl residue ((MeO)2Tr), and phosphonate 4 as well as phosphoramidite 5 were prepared under standard conditions. Phosphonate 4 was employed in solid-phase oligonucleotide synthesis. Homooligonucleotides as well as self-complementary oligonucleotides were prepared. The oligomer d[(N7A)11-A] (11) formed a duplex with d(T12) (13). Antiparallel chain polarity and reverse Watson-Crick base pairing was deduced from duplex formation of the self-complementary d[(N7A)8-T8] (14).
- Seela,Winter
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p. 597 - 607
(2007/10/02)
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- Ionization of purine nucleosides and nucleotides and their components by 193-nm laser photolysis in aqueous solution: Model studies for oxidative damage of DNA 1
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The effect of 20-ns pulses of 193-nm laser light on aqueous solutions of purine bases, (2′-deoxy)nucleosides, and (2′-deoxy)nucleotides was investigated, and monophotonic ionization was observed. Although (deoxy)ribose and (deoxy)ribose phosphates are also ionized by 193-nm light, the photoionization of the (deoxy)nucleosides and -tides takes place predominantly (90%) at the purine moiety, due to the much higher extinction coefficients at 193 nm of the bases as compared to the (deoxy)ribose phosphates. The quantum yields of photoionization (φPl) of the purines are in the range 0.01 to 0.08, based on φ(Cl-) at 193 nm of 0.46. As shown by comparison with data obtained from pulse radiolysis, the ionized purines, i.e., the radical cations, deprotonate in neutral solution, yielding neutral radicals. The radical cation of 1-methylguanosine, produced by photoionization in oxygen-saturated aqueous solution, deprotonates with the rate constant 3.5 × 105 s-1. In the absence of oxygen, the hydrated electrons resulting from the photoionization react with the untransformed purine derivatives to yield the corresponding radical anions. As these are rapidly protonated by water (as concluded from pulse radiolysis), the photoionization in deaerated neutral solution results in two different neutral radicals: a deprotonated radical cation and a protonated radical anion.
- Candeias,Steenken
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p. 699 - 704
(2007/10/02)
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- Deoxyribose-5-phosphate aldolase as a catalyst in asymmetric aldol condensation
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This paper describes the substrate specificity and synthetic utility of deoxyribose-5-phosphate aldolase (DERA, EC 4.1.2.4). Eight donors and 20 acceptors have been tested as substrates. In addition to acetaldehyde, propanal, acetone, and fluoroacetone have been used to condense with a number of acceptor aldehydes. Thirteen aldol products have been prepared and characterized. A new stereogenic center with 3(S) configuration is formed when acetaldehyde, fluoroacetone, or acetone is used as a donor substrate. With propanal, two new stereogenic centers are formed with 2(R) and 3(S) configurations. The acceptor substrates have very little structural requirements. The 2-hydroxyaldehydes appear to react the fastest, and the D-isomers are better substrates than the L-isomers. The stereospecificity is absolute regardless of the chirality of 2-hydroxyaldehydes. The aldol reactions thus follow the Cram-Felkin mode of attack for D-substrates and anti-Cram-Felkin mode of attack for L-substrates.
- Chen, Lihren,Dumas, David P.,Wong, Chi-Huey
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p. 741 - 748
(2007/10/02)
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- Highly Stereoselective Total Synthesis of 2,5-Anhydro-3-deoxy- and -4-deoxy-D-hexonic Acids and of the Related Deoxyadenosines-C
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(1R,2S,4R)-2-Cyano-7-oxabicyclohept-5-en-2-yl (1S')-camphanate (5) has been converted into 2,5-anhydro-3-deoxy-D-ribo-hexonic acid (8, eight steps, 38percent) and 2,5-anhydro-3-deoxy-D-xylo-hexonic acid (9, seven steps, 40percent).Similarly, (1S,4S)-7-oxabicyclohept-5-en-3-one ((-)-6, derived from (1S,2R,4S)-2-cyano-7-oxabicyclohept-5-en-2-yl (1R')-camphanate (7) was converted into 2,5-anhydro-4-deoxy-D-ribo-hexonic acid (10, nine steps, 29percent) and 2,5-anhydro-4-deoxy-D-xylo-hexonic acid (11, eight steps, 31percent).The methods exploit the high regioselectivity of the electrophilic additions of the C=C double bonds in 7-oxabicyclohept-5-en-2-yl derivatives 5 and 7 ("naked sugars") and the high exo-face preference for the hydride reduction of 5- and 6-chloro-7-oxabicyclohept-5-en-2-ones (21,35). 2'-Deoxyadenosine-C (12) and cordycepin-C (14) were derived from 8 and 10, respectively.Similarly, the corresponding 2'- and 3'-epimers 13 and 15 (C-nucleosides deriving from 2-deoxy- and 3-deoxy-β-D-threo-pentofuranose, respectively) were obtained in few steps and with high stereoselectivity from 9 and 11, respectively.
- Gasparini, Fabrizio,Vogel, Pierre
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p. 2451 - 2457
(2007/10/02)
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- Stereoselective Synthesis of 2-Amino-2-deoxy-D-arabinose and 2-Deoxy-D-ribose
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An efficient method for the stereoselective synthesis of 2-amino-2-deoxy-D-arabinose and 2-deoxy-D-ribose is described.The key step in this method was accomplished by the nucleophilic addition of methyl isocyanoacetate to 2,3-O-isopropylidene-D-glyceraldehyde with high erythro-selectivity (nearly 100percent).Subsequent intermolecular cyclization predominantly gave the desired oxazoline derivative (trans-form), in which two new chiral centers were formed.The oxazoline derivative was efficiently converted to both 2-amino-2-deoxy-D-arabinose and 2-deoxy-D-ribose.
- Yamamoto, Yoshihiro,Kirihata, Mitsunori,Ichimoto, Itsuo,Ueda, Hiroo
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p. 1435 - 1440
(2007/10/02)
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- SILYL NITRONATES AND NITRILE OXIDES IN ORGANIC SYNTHESIS. A NOVEL ROUTE TO D,L-DEOXYSUGARS. USE OF ALUMINIUM OXIDE AS SOLID PHASE BASE FOR GENERATION OF NITRILE OXIDES FROM HYDROXIMIC ACID CHLORIDES
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Novel methodology is developed for a three step synthesis of deoxyaldoses and deoxyketoses. 1.Regioselective addition of silyl nitronate or nitrile oxide to a diene. 2.Stereospecific hydroxylation of the double bond. 3.Unmasking of the aldol moiety by catalytic reduction of the 2-isoxazoline.The syntheses of D.L-deoxyribose, D,L-oleose, D,L-digitoxose, D,L-2-deoxygalactose, 1,3-dideoxyfructose, 3-deoxyfructose etc. are described.Basic aluminium oxide is introduced as a solid phase base for the one step synthesis of 2-isoxazolines from aldoximes and olefins.An X-ray diffraction study of compound 13c verifies the stereochemical assignments.
- Torssell, K. B. G.,Hazell, A. C.,Hazell, R. G.
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p. 5569 - 5576
(2007/10/02)
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- THE CHEMISTRY OF O-SILYLATED KETENE ACETALS; DIASTEREOSELECTIVE ALDOL REACTION OF 2,3-O-ISOPROPYLIDENE-D (AND L)-GLYCERALDEHYDES LEADING TO 2-DEOXY-D (AND L)-RIBOSES
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Diastereoselective carbon-carbon bond forming reaction of 2,3-O-isopropylidene-D (and L)-glyceraldehydes (D and L-2) with ketene silyl acetals (1a,b) occured in acetonitrile under mild conditions to give the corresponding anti-β-siloxyesters (D and L-3a) as major products, which could be converted through a few additional steps to 2-deoxy-D (and L)-riboses.
- Kita, Yasuyuki,Yasuda, Hitoshi,Tamura, Osamu,Itoh, Fumio,Ke, Ya Yuan,Tamura, Yasumitsu
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p. 5777 - 5780
(2007/10/02)
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- A NEW METHOD FOR THE GENERATION OF A BORON ENOLATE OF AN ESTER - A NEW SYNTHESIS OF 2-DEOXY-D-RIBOSE -
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A boron enolate of an ester was generated in situ by the treatment of ethoxyacetylene with mercury(II) acetate and diphenylborinic acid, and the boron enolate thus formed further reacted with aldehydes to give β-hydroxyesters and β-acetoxyesters in good yields.The reaction was successfully applied to the stereoselective synthesis of 2-deoxy-D-ribose.
- Murakami, Masahiro,Mukaiyama, Teruaki
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p. 241 - 244
(2007/10/02)
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- Synthesis of 2-Deoxy-(+/-)-erythropentose (Deoxyribose)
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Action of N-bromosuccinimide on 1,3:2,4-di-O-benzylideneerythritol furnished 3-O-benzoyl-2,4-O-benzylidene-1-bromo-1-deoxy-DL-erythritol (II) which on reaction with NaCN is transformed into 4-O-benzoyl-3,5-O-benzylidene-2-deoxy-DL-erythropentanonitrile (I
- Bhat, K. S.,Rao, A. S.
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p. 140 - 141
(2007/10/02)
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- A CONVENIENT SYNTHESIS OF 2-DEOXY-D-RIBOSE
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Successive treatment of allyltin difluoroiodide, formed in situ by the oxidative addition of stannous fluoride to allyliodide, with 1,2-O-isopropylidene-D-glyceraldehyde and phenoxyacetyl chloride results in the predominant formation of erythro homoallyle
- Harada, Taira,Mukaiyama, Teruaki
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p. 1109 - 1110
(2007/10/02)
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