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1.
Org Biomol Chem ; 15(15): 3196-3201, 2017 Apr 11.
Artigo em Inglês | MEDLINE | ID: mdl-28362446

RESUMO

The efficient transformation of benzylamines into the corresponding oximes has been described by means of a chemoenzymatic process. This strategy is based on a two-step sequence developed in one-pot at 30 °C and atmospheric pressure. First, the formation of a reactive peracid intermediate occurs by means of a lipase-catalysed perhydrolysis reaction, and then this peracid acts as a chemical oxidising agent of the amines. A total of nine ketoximes were isolated in high purity after a simple extraction protocol (90-98% isolated yield), while for the eleven synthesised aldoximes a further column chromatography purification was required (71-82% isolated yield). In all cases excellent selectivities were attained, offering a practical method for amine oxidation in short reaction times (1 hour). The environmental impact of the process was analysed and compared with a recently published alternative chemical synthesis, finding for this metric a good E-factor value.

2.
J Org Chem ; 81(20): 9765-9774, 2016 10 21.
Artigo em Inglês | MEDLINE | ID: mdl-27662230

RESUMO

Two independent enzymatic strategies have been developed toward the synthesis of enantioenriched 1-[2-bromo(het)aryloxy]propan-2-amines. With that purpose a series of racemic amines and prochiral ketones have been synthesized from commercially available 2-bromophenols or brominated pyridine derivatives bearing different pattern substitutions in the aromatic ring. Biotransamination experiments have been studied using ketones as starting materials, yielding both the (R)- and (S)-amine enantiomers with high selectivity (91-99% ee) depending on the transaminase source. In a complementary approach, the classical kinetic resolutions of the racemic amines have been investigated using Candida antarctica lipase type B as biocatalyst. Ethyl methoxyacetate was found as a suitable acyl donor leading to the corresponding (S)-amines (90-99% ee) and (R)-amides (88-99% ee) with high selectivity in most of the cases. A preparative biotransamination process has been developed for the synthesis of (2S)-1-(6-bromo-2,3-difluorophenoxy)propan-2-amine in 61% isolated yield after 24 h, a valuable precursor of the antimicrobial agent Levofloxacin.

3.
Angew Chem Int Ed Engl ; 55(9): 3144-7, 2016 Feb 24.
Artigo em Inglês | MEDLINE | ID: mdl-26836037

RESUMO

Transaminases are valuable enzymes for industrial biocatalysis and enable the preparation of optically pure amines. For these transformations they require either an amine donor (amination of ketones) or an amine acceptor (deamination of racemic amines). Herein transaminases are shown to react with aromatic ß-fluoroamines, thus leading to simultaneous enantioselective dehalogenation and deamination to form the corresponding acetophenone derivatives in the absence of an amine acceptor. A series of racemic ß-fluoroamines was resolved in a kinetic resolution by tandem hydrodefluorination/deamination, thus giving the corresponding amines with up to greater than 99 % ee. This protocol is the first example of exploiting the catalytic promiscuity of transaminases as a tool for novel transformations.


Assuntos
Flúor/química , Transaminases/química , Catálise , Cristalografia por Raios X , Desaminação , Escherichia coli/genética , Transaminases/genética
4.
J Org Chem ; 80(8): 3815-24, 2015 Apr 17.
Artigo em Inglês | MEDLINE | ID: mdl-25786159

RESUMO

A versatile and general route has been developed for the asymmetric synthesis of a wide family of 3-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazines bearing different pattern substitutions in the aromatic ring. Whereas hydrolases were not suitable for resolution of these racemic cyclic nitrogenated amines, alternative chemoenzymatic strategies were designed through independent pathways leading to both amine antipodes. On one hand, bioreduction of 1-(2-nitrophenoxy)propan-2-ones allowed the recovery of the enantiopure (S)-alcohols in high yields using the alcohol dehydrogenase from Rhodococcus ruber (ADH-A), whereas evo-1.1.200 ADH led to their counterpart (R)-enantiomers also with complete selectivity and quantitative conversion. Alternatively, lipase-catalyzed acetylation of these racemic alcohols, and the complementary hydrolysis of the acetate analogues, gave access to the corresponding optically enriched products with high stereodiscrimination. Particularly attractive was the design of a chemoenzymatic strategy in six steps for the production of (S)-(-)-7,8-difluoro-3-methyl-3,4-dihydro-2H-benzo-[b][1,4]oxazine, which is a key precursor of the antimicrobial agent Levofloxacin.


Assuntos
Anti-Infecciosos/síntese química , Benzoxazinas/síntese química , Levofloxacino/síntese química , Anti-Infecciosos/química , Benzoxazinas/química , Catálise , Levofloxacino/química , Estrutura Molecular , Estereoisomerismo
5.
Org Biomol Chem ; 12(4): 673-81, 2014 Jan 28.
Artigo em Inglês | MEDLINE | ID: mdl-24302226

RESUMO

Lactobacillus brevis ADH (LBADH) is an alcohol dehydrogenase that is commonly employed to reduce alkyl or aryl ketones usually bearing a methyl, an ethyl or a chloromethyl as a small ketone substituent to the corresponding (R)-alcohols. Herein we have tested a series of 24 acetophenone derivatives differing in their size and electronic properties for their reduction employing LBADH. After plotting the relative activity against the measured substrate volumes we observed that apart from the substrate size other effects must be responsible for the activity obtained. Compared to acetophenone (100% relative activity), other small substrates such as propiophenone, α,α,α-trifluoroacetophenone, α-hydroxyacetophenone, and benzoylacetonitrile had relative activities lower than 30%, while medium-sized ketones such as α-bromo-, α,α-dichloro-, and α,α-dibromoacetophenone presented relative activities between 70% and 550%. Moreover, the comparison between the enzymatic activity and the obtained final conversions using an excess or just 2.5 equiv. of the hydrogen donor 2-propanol, denoted again deviations between them. These data supported that these hydrogen transfer (HT) transformations are mainly thermodynamically controlled. For instance, bulky α-halogenated derivatives could be quantitatively reduced by LBADH even employing 2.5 equiv. of 2-propanol independently of their kinetic values. Finally, we found good correlations between the IR absorption band of the carbonyl groups and the degrees of conversion obtained in these HT processes, making this simple method a convenient tool to predict the success of these transformations.


Assuntos
Álcool Desidrogenase/metabolismo , Álcoois/metabolismo , Cetonas/metabolismo , Levilactobacillus brevis/enzimologia , Álcool Desidrogenase/química , Álcoois/química , Elétrons , Cetonas/química , Modelos Moleculares , Estrutura Molecular , Oxirredução
6.
Bioorg Med Chem ; 22(20): 5563-8, 2014 Oct 15.
Artigo em Inglês | MEDLINE | ID: mdl-24890654

RESUMO

The lipase catalyzed resolution of cis and trans-3-amino-4-hydroxytetrahydrofurans and cis-3-amino-4-hydroxypyrrolidines have been studied. For all the heterocycles, the best enantioselectivity was obtained using Candida antarctica lipases A and B as catalysts in hydrolytic processes. The absolute configuration of the optically pure obtained heterocycles has been assigned.


Assuntos
Candida/enzimologia , Furanos/metabolismo , Lipase/metabolismo , Pirrolidinas/metabolismo , Biocatálise , Candida/metabolismo , Furanos/química , Hidrólise , Estrutura Molecular , Pirrolidinas/química , Estereoisomerismo
7.
Chemistry ; 19(3): 892-904, 2013 Jan 14.
Artigo em Inglês | MEDLINE | ID: mdl-23197418

RESUMO

An exhaustive experimental study based on X-ray diffraction analysis, NMR, FTIR-ATR (attenuated total reflection), and Raman spectroscopy as well as theoretical calculations is reported in order to understand how the non-covalent intermolecular contacts are fundamental to explain structure-property relationships and allowing us to correlate a basic macroscopic property (i.e., the melting point, T(m)) with the structural variables of a family of enantiopure 1,4-dialkyl-1,2,4-triazolium salts. The effect of different structural vectors such as the ring size, the spatial disposition of the substituent, the substitution on the oxygen atom, the nature of the anion, or the N4 alkylation of the triazole on the intermolecular interactions of these chiral salts of a well-defined 3D structure is reported. The non-covalent intermolecular contacts mainly implicating the triazolium H3 proton are fundamental to explain structure-property relationships and, therefore, the physical properties of these new chiral salts, rather than simple anion-cation interactions. Overall, our findings highlight the importance of the specific supramolecular interactions for the understanding of the physical properties of triazolium salts and ionic liquids.


Assuntos
Líquidos Iônicos/química , Triazóis/química , Substâncias Macromoleculares/química , Modelos Moleculares , Estrutura Molecular , Sais/química
8.
J Org Chem ; 78(14): 7312-7, 2013 Jul 19.
Artigo em Inglês | MEDLINE | ID: mdl-23796348

RESUMO

The use of purified and overexpressed alcohol dehydrogenases to synthesize enantiopure fluorinated alcohols is shown. When the bioreductions were performed with ADH-A from Rhodococcus ruber overexpressed in E. coli, no external cofactor was necessary to obtain the enantiopure (R)-derivatives. Employing Lactobacillus brevis ADH, it was possible to achieve the synthesis of enantiopure (S)-fluorohydrins at a 0.5 M substrate concentration. Furthermore, due to the activated character of these substrates, a huge excess of the hydrogen donor was not necessary.


Assuntos
Álcool Desidrogenase/metabolismo , Hidrocarbonetos Fluorados/metabolismo , Rhodococcus/enzimologia , Hidrocarbonetos Fluorados/química , Estrutura Molecular
9.
Bioorg Med Chem ; 21(24): 7779-89, 2013 Dec 15.
Artigo em Inglês | MEDLINE | ID: mdl-24216092

RESUMO

C-3-substituted 25-hydroxyvitamin D3 analogues were synthesized as tools to directly measure levels of vitamin D in biological samples. The strategy involves vinyloxycarbonylation of the 3ß-hydroxy group and formation of a carbamate bond with a hydroxyl or amino group at the end of the alkyl chain. Biotinylated conjugates of synthesized derivatives were generated to be linked with vitamin D binding protein (DBP). The spacer group present in the alkyl chain is important in the binding of antibodies to the analogue-DBP complex. When compared to 25-hydroxyvitamin D3-DBP, the binding of some antibodies to the analogue-DBP complex of the 25-hydroxyvitamin D3 derivative 10 that posses an 8-aminoctyl alkyl chain is significantly reduced, but this analogue displaced [26,27-(3)H]-25-hydroxyvitamin D3 from DBP. In contrast, the 8-hydroxyoctyl alkyl chain analogue 9 showed less displacement.


Assuntos
Calcifediol/síntese química , Vitamina D/sangue , Calcifediol/análogos & derivados , Calcifediol/sangue , Calcifediol/química , Humanos , Conformação Molecular
10.
J Org Chem ; 77(10): 4842-8, 2012 May 18.
Artigo em Inglês | MEDLINE | ID: mdl-22515546

RESUMO

A chemoenzymatic asymmetric route for the preparation of enantiopure (R)-ramatroban has been developed for the first time. The action of lipases and oxidoreductases has been independently studied, and both were found as excellent biocatalysts for the production of adequate chiral intermediates under very mild reaction conditions. CAL-B efficiently catalyzed the resolution of (±)-2,3,4,9-tetrahydro-1H-carbazol-3-ol that was acylated with high stereocontrol. On the other hand, ADH-A mediated bioreduction of 4,9-dihydro-1H-carbazol-3(2H)-one provided an alternative access to the same enantiopure alcohol previously obtained through lipase-catalyzed resolution, a useful synthetic building block in the synthesis of ramatroban. Inversion of the absolute configuration of (S)-2,3,4,9-tetrahydro-1H-carbazol-3-ol has been identified as a key point in the synthetic route, optimizing this process to avoid racemization of the azide intermediate, finally yielding (R)-ramatroban in enantiopure form by the formation of the corresponding amine and the convenient functionalization of both exocyclic and indole nitrogen atoms.


Assuntos
Carbazóis/química , Carbazóis/síntese química , Lipase/química , Lipase/metabolismo , Nitrogênio/química , Oxirredutases/química , Oxirredutases/metabolismo , Sulfonamidas/química , Sulfonamidas/síntese química , Acilação , Catálise , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Estereoisomerismo
11.
J Org Chem ; 77(18): 8049-55, 2012 Sep 21.
Artigo em Inglês | MEDLINE | ID: mdl-22917174

RESUMO

Racemic indolines including a variety of structural motifs such as C-2 and C-3 substitutions (alkyl or aryl), cis/trans relative stereochemistry and functionalization of the aromatic ring (fluoro, methyl or methoxy groups) have been efficiently prepared through Fischer indolization and subsequent diastereoselective reduction of the unprotected indoles. Combination of Candida antarctica lipase type A and allyl 3-methoxyphenyl carbonate has been identified as the best tandem for their kinetic resolutions, observing excellent stereodiscriminations for most of the tested indolines.


Assuntos
Candida/enzimologia , Indóis/síntese química , Lipase/química , Candida/química , Catálise , Indóis/química , Lipase/metabolismo , Estrutura Molecular , Estereoisomerismo
12.
J Org Chem ; 77(10): 4671-8, 2012 May 18.
Artigo em Inglês | MEDLINE | ID: mdl-22551299

RESUMO

Several novel nucleoside analogues as potential inhibitors of glycosidases and purine nucleoside phosphorylase (PNP) have been synthesized via selective coupling of an appropriate nucleobase at different positions of an orthogonally protected imino sugar as a common precursor. This synthetic strategy offers a straightforward protocol for the assembly of imino sugar containing nucleosides, establishing a new repertoire of molecules as potential therapeutics.


Assuntos
Glicosídeo Hidrolases/antagonistas & inibidores , Imino Açúcares/química , Nucleosídeos/química , Nucleosídeos/síntese química , Purina-Núcleosídeo Fosforilase/antagonistas & inibidores , Pirrolidinas/síntese química , Sulfonamidas/síntese química , Pareamento de Bases , Glicosídeo Hidrolases/química , Glicosídeo Hidrolases/metabolismo , Humanos , Espectroscopia de Ressonância Magnética , Purina-Núcleosídeo Fosforilase/química , Purina-Núcleosídeo Fosforilase/metabolismo , Pirrolidinas/química , Sulfonamidas/química
13.
Bioorg Med Chem Lett ; 22(13): 4310-3, 2012 Jul 01.
Artigo em Inglês | MEDLINE | ID: mdl-22647722

RESUMO

Several acyl derivatives of the aureolic acid chromomycin A(3) were obtained via lipase-catalyzed acylation. Lipase B from Candida antarctica (CAL-B) was found to be the only active biocatalyst, directing the acylation regioselectively towards the terminal secondary hydroxyl group of the aglycone side chain. All new chromomycin A(3) derivatives showed antitumor activity at the micromolar or lower level concentration. Particularly, chromomycin A(3) 4'-vinyladipate showed 3-5 times higher activity against the four tumor cell lines assayed as compared to chromomycin A(3).


Assuntos
Antineoplásicos/síntese química , Cromomicina A3/análogos & derivados , Lipase/metabolismo , Acilação , Animais , Antineoplásicos/química , Antineoplásicos/toxicidade , Biocatálise , Candida/enzimologia , Linhagem Celular Tumoral , Cromomicina A3/síntese química , Cromomicina A3/toxicidade , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Camundongos , Células NIH 3T3 , Estereoisomerismo
14.
Bioorg Med Chem ; 20(23): 6885-93, 2012 Dec 01.
Artigo em Inglês | MEDLINE | ID: mdl-23085031

RESUMO

A series of 2',3'-dideoxy-2',2'-difluoro-4'-azanucleosides of both pyrimidine and purine nucleobases were synthesized in an efficient manner starting from commercially available L-pyroglutamic acid via glycosylation of difluorinated pyrrolidine derivative 15. Several 4'-azanucleosides were prepared as a separable mixture of α- and ß-anomers. The 6-chloropurine analogue was obtained as a mixture of N(7) and N(9) regioisomers and their structures were identified based on NOESY and HMBC spectral data. Among the 4'-azanucleosides tested as HIV-1 inhibitors in primary human lymphocytes, four compounds showed modest activity and the 5-fluorouracil analogue (18d) was found to be the most active compound (EC(50)=36.9µM) in this series. None of the compounds synthesized in this study demonstrated anti-HCV activity.


Assuntos
Antivirais/química , Antivirais/farmacologia , HIV-1/efeitos dos fármacos , Hepacivirus/efeitos dos fármacos , Nucleosídeos/química , Nucleosídeos/farmacologia , Antivirais/síntese química , Antivirais/toxicidade , Compostos Aza/síntese química , Compostos Aza/química , Compostos Aza/farmacologia , Compostos Aza/toxicidade , Infecções por HIV/tratamento farmacológico , Halogenação , Hepatite C/tratamento farmacológico , Humanos , Leucócitos Mononucleares/efeitos dos fármacos , Leucócitos Mononucleares/virologia , Nucleosídeos/síntese química , Nucleosídeos/toxicidade
15.
Anal Bioanal Chem ; 402(5): 1879-88, 2012 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-22241580

RESUMO

A novel and fast routine method for the simultaneous determination and confirmation of clenbuterol in bovine and human urine samples by gas chromatography electron ionization mass spectrometry (GC-EI-MS) has been developed. The method employs isotope dilution mass spectrometry (IDMS) and is based on a combination of minimal labeling (a single (13)C label in the molecule) and isotope pattern deconvolution (IPD). This new methodology does not require the construction of a methodological calibration graph, and was compared with the classical IDMS procedure employed in clenbuterol analysis based on the use of a deuterated compound as internal standard (d(9)-clenbuterol) and a calibration curve. The sample preparation consists of simple extraction with dichloromethane, which was dried and derivatized with chloro(chloromethyl)dimethylsilane, generating a cyclic dimethylsilamorpholine (DMS) derivative suitable for GC(EI)MS detection and identification. This compound produces five intense ions in the electron ionization source, which allow the presence of clenbuterol to be confirmed in just one analysis, as demanded by European Union directives. The accuracy of the method was studied by performing recovery experiments at different concentration levels (from 0.3 to 5 ng g(-1)) in 5 mL bovine urine samples using two labeled compounds: an in-house-synthesized (13)C(1)-clenbuterol and a commercially available d(9)-clenbuterol. The detection limit of the method in human urine was 0.050 ng g(-1) with a sample volume of 10 mL, and is thus suitable for antidoping control purposes. Finally, the (13)C(1)-clenbuterol standard was employed for the determination of clenbuterol in two reference materials, BCR-503 and BCR-504 (lyophilized bovine urine). The concentrations obtained were in agreement with the certified values, with a reproducibility of below 1% RSD.


Assuntos
Clembuterol/urina , Cromatografia Gasosa-Espectrometria de Massas/métodos , Espectrometria de Massas por Ionização por Electrospray/métodos , Animais , Calibragem , Isótopos de Carbono , Bovinos , Humanos , Marcação por Isótopo , Limite de Detecção , Padrões de Referência , Reprodutibilidade dos Testes , Sensibilidade e Especificidade
16.
J Org Chem ; 76(3): 811-9, 2011 Feb 04.
Artigo em Inglês | MEDLINE | ID: mdl-21218800

RESUMO

Desymmetrizaton enzymatic processes have been extensively studied searching for optimal methods of producing enantioenriched monoacetates from prochiral diols and diesters. AK lipase has been found as an excellent biocatalyst for the desymmetriaztion of a series of previously synthesized 3-arylpentane-1,5-diols derivatives. The access to (S)- or (R)-monoacetates in high optical purity (86-99% ee) has been possible by using acetylation or hydrolysis reactions, respectively, where the reaction parameters have been optimized in terms of source and amount of biocatalyst, temperature, solvent, and reaction time. The synthetic potential of enantiopure monoesters has been demonstrated by using these interesting chiral building blocks for the preparation of novel enantiopure carboxylic acid derivatives.


Assuntos
Ácidos Carboxílicos/química , Lipase/química , Catálise , Estrutura Molecular , Rotação Ocular , Solventes/química , Estereoisomerismo , Temperatura
17.
J Org Chem ; 76(14): 5709-18, 2011 Jul 15.
Artigo em Inglês | MEDLINE | ID: mdl-21627134

RESUMO

A novel family of prochiral pentane-1,5-diamines has been efficiently synthesized, possessing stabilities significantly higher than those of corresponding propane-1,3-diamine analogues. Diamines have been later desymmetrized using Pseudomonas cepacia lipase as an efficient biocatalyst for the mono- but also stereoselective protection of one of their amino groups. Reaction parameters such as type and loading of enzyme, temperature, solvent, and acyl donor have been exhaustively analyzed, searching for optimal conditions for the production of interesting optically active nitrogenated compounds. Thus, acylation and alkoxycarbonylation processes have been compared in terms of conversion and enantiomeric excess values. The best results were found in the reaction of prochiral diamines with ethyl methoxyacetate as acyl donor and 1,4-dioxane as solvent, yielding (S)-monoamides in 33-59% isolated yield and 54-99% ee, depending on the aromatic pattern substitution.


Assuntos
Cadaverina/biossíntese , Lipase/metabolismo , Biocatálise , Burkholderia cepacia/enzimologia , Cadaverina/síntese química , Cadaverina/química , Lipase/química , Estrutura Molecular , Estereoisomerismo
18.
J Org Chem ; 76(7): 2115-22, 2011 Apr 01.
Artigo em Inglês | MEDLINE | ID: mdl-21384803

RESUMO

A simple and novel chemoenzymatic route has been applied for the first time in the synthesis of miconazole and econazole single enantiomers. Lipases and oxidoreductases have been tested in stereoselective processes; the best results were attained with oxidoreductases for the introduction of chirality in an adequate intermediate. The behaviors of a series of ketones and racemic alcohols in bioreductions and acetylation procedures, respectively, have been investigated; the best results were found with alcohol dehydrogenases A and T, which allowed the production of (R)-2-chloro-1-(2,4-dichlorophenyl)ethanol in enantiopure form under very mild reaction conditions. Final chemical modifications have been performed in order to isolate the target fungicides miconazole and econazole both as racemates and as single enantiomers. Biological evaluation of the racemates and single enantiomers has shown remarkable differences against the growth of several microorganisms; while (R)-miconazole seemed to account for most of the biological activity of racemic miconazole on all the strains tested, both enantiomers of econazole showed considerable biological activities. In this manner, (R)-econazole showed higher values against Candida krusei , while higher values were observed for (S)-econazole against Cryptococcus neoformans, Penicillium chrysogenum, and Aspergillus niger.


Assuntos
Antifúngicos/síntese química , Antifúngicos/farmacologia , Econazol/síntese química , Econazol/farmacologia , Hidrocarbonetos Clorados/química , Hidrocarbonetos Clorados/síntese química , Lipase/química , Miconazol/síntese química , Miconazol/farmacologia , Animais , Antifúngicos/química , Candida/química , Candida/efeitos dos fármacos , Econazol/química , Humanos , Espectroscopia de Ressonância Magnética , Miconazol/química , Testes de Sensibilidade Microbiana , Estrutura Molecular , Estereoisomerismo
19.
Org Biomol Chem ; 9(7): 2274-8, 2011 Apr 07.
Artigo em Inglês | MEDLINE | ID: mdl-21308130

RESUMO

Because of the importance of developing stereoselective syntheses for single enantiomers, a selected panel of racemic biologically active 1-aryl- and 1-heteroarylpropan-2-amines has been prepared, followed by a study of their behavior in enzymatic kinetic resolution (KR) processes. For this purpose, lipase B from Candida antarctica (CAL-B) proved to be an ideal biocatalyst allowing the preparation of the corresponding enantioenriched (R)-amides and (S)-amines by aminolysis reactions. Likewise, dynamic kinetic resolutions (DKR) have been successfully achieved combining the use of CAL-B and Shvo's catalyst. This research constitutes the first example of a lipase-catalyzed DKR process of ß-substituted isopropylamines.


Assuntos
Aminas/química , Propano/química , Aminas/metabolismo , Candida/enzimologia , Proteínas Fúngicas , Cinética , Lipase/metabolismo , Estrutura Molecular , Estereoisomerismo
20.
Org Biomol Chem ; 9(17): 5960-6, 2011 Sep 07.
Artigo em Inglês | MEDLINE | ID: mdl-21748181

RESUMO

Preparation of abasic site precursors through a divergent chemoenzymatic synthesis has been accomplished. Several biocatalysts and acylating agents were studied furnishing a practical and scalable green method useful for industrial applications. Highly regioselective acylation and deacylation reactions with 1,2-dideoxy-D-ribose are described resulting in excellent yield. A fast, atom-efficient and convenient synthesis of 3-, and 5-O-DMTr-1,2-dideoxyribose 17 and 19 has been achieved. These compounds are useful precursors for the preparation of phosphoramidites required for the assembly of oligonucleotides containing the tetrahydrofuran abasic lesions.


Assuntos
Desoxirribose/análogos & derivados , Química Verde/métodos , Oligonucleotídeos/síntese química , Acilação , Biocatálise , Chromobacterium/enzimologia , Desoxirribose/química , Desoxirribose/metabolismo , Lipase/metabolismo , Oligonucleotídeos/metabolismo , Pseudomonas/enzimologia
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