Nucleobase Protection of Deoxyribo‐ and Ribonucleosides

Meher, Geeta; Meher, Nabin K.; Iyer, Radhakrishnan P.

doi:10.1002/cpnc.32

Cited by 10 publications

(7 citation statements)

References 295 publications

(270 reference statements)

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“…In recent years, applications of ODNs have extended to emerging areas such as nanotechnology [8–9], antisense drug development [10–12], DNA damage and repair [13–14], DNA methylation and demethylation [15–18], DNA–protein interactions [19–20], CRISPR genome editing [21–23], DNA data storage [24–25], synthetic biology [26], bioconjugation [27] and others [28–30]. These applications frequently require modified ODNs that contain a wide variety of functional groups including those that cannot survive known ODN synthesis, cleavage and deprotection conditions.…”

Section: Introductionmentioning

confidence: 99%

“…These applications frequently require modified ODNs that contain a wide variety of functional groups including those that cannot survive known ODN synthesis, cleavage and deprotection conditions. To meet these demands, some work on developing new technologies suitable for the synthesis of sensitive ODNs has been carried out [28,31]. A common method is to use more labile acyl functions such as the phenoxyacetyl group for amino protection and as linker to enable deprotection and cleavage under milder basic conditions [32].…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Electrophilic oligodeoxynucleotide synthesis using dM-Dmoc for amino protection

Shahsavari¹,

Eriyagama²,

Halami³

et al. 2019

Beilstein J. Org. Chem.

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Solid-phase synthesis of electrophilic oligodeoxynucleotides (ODNs) was achieved using dimethyl-Dmoc (dM-Dmoc) as amino protecting group. Due to the high steric hindrance of the 2-(propan-2-ylidene)-1,3-dithiane side product from deprotection, the use of excess nucleophilic scavengers such as aniline to prevent Michael addition of the side product to the deprotected ODN during ODN cleavage and deprotection was no longer needed. The improved technology was demonstrated by the synthesis and characterization of five ODNs including three modified ones. The modified ODNs contained the electrophilic groups ethyl ester, α-chloroamide, and thioester. Using the technology, the sensitive groups can be installed at any location within the ODN sequences without using any sequence- or functionality-specific conditions and procedures.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Electrophilic oligodeoxynucleotide synthesis using dM-Dmoc for amino protection

Shahsavari¹,

Eriyagama²,

Halami³

et al. 2019

Beilstein J. Org. Chem.

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“…For modified ODNs, we still face many challenges. [14][15][16][17][18][19][20][21][22][23] In one particular case, due to the use of acyl protecting groups and linkers during solid phase synthesis and their need of strong nucleophiles for deprotection and cleavage, many nucleophile-sensitive groups could not be incorporated into this highly important class of materials. Examples of the sensitive groups include many common ones in organic chemistry such as esters, alkyl halides and epoxides.…”

Section: Introductionmentioning

confidence: 99%

Incorporation of Sensitive Ester and Chloropurine Groups into Oligodeoxynucleotides through Solid‐Phase Synthesis

et al. 2018

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Nucleosides containing ester groups that are sensitive to nucleophiles were incorporated into oligodeoxynucleotides (ODNs) through solid phase chemical synthesis. The sensitive esters are located on a purine nucleobase. They are the esters of ethyl, 2‐methoxyethyl, 4‐methoxyphenyl and phenyl groups, and a thioester. These esters cannot survive the deprotection and cleavage conditions used in known ODN synthesis technologies, which involve strong nucleophiles such as ammonium hydroxide and potassium methoxide (potassium carbonate in anhydrous methanol). To incorporate these sensitive groups into ODNs, the Dmoc (i. e. dimethyl‐1,3‐dithian‐2‐ylmethoxycarbonyl) phosphoramidites and linker were used for solid phase synthesis, which allowed ODN deprotection and cleavage to be carried out under non‐nucleophilic oxidative conditions. Sixteen ODN sequences containing these groups were synthesized and characterized with MALDI MS. In addition, the synthesis and characterization of three ODNs containing a nucleophile sensitive 6‐chloropurine using the same strategy are described.

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“…Bio-diesel production can also be carried out by homogeneous alkali, acid and enzyme [16][17][18][19][20][21][22][23][24][25] . The use of FAME plays a positive and important role in solving the problems of energy shortage and the pollution in a period of time.…”

Section: Introductionmentioning

confidence: 99%

PRODUCTION OF NON-ESTER RENEWABLE DIESEL BY THE HYDROGENATION OF VEGETABLE OIL ON THE 15Co5Ni-10Ce / Al2O3 CATALYST

Huang

Zhang

2015

J. Chil. Chem. Soc.

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The catalysts by incipient wetness impregnation method were prepared and characterized by XRD, BET, H 2 -TPD, NH 3 -TPD and H 2 -TPR analysis, and the catalyst activity was detected by WFSM-3060 high-pressure reactor. Effective double metal catalysts were produced by using γ-Al 2 O 3 as carrier and Co and Ni as activity center, and more effectiveness by using Ce to modify. The results revealed that the 15Co5Ni-10Ce catalyst was the best in producing bio-fuels. The catalyst had good thermal stability, three kinds of adsorbed sites and three kinds of acidic sites. Compared with sintering, the catalyst deactivation was due to coke deposition. The results of FT -IR, SF-3, GC and GC-MS indicated that reaction temperature is the key factor and that oil velocity is a very important factor. The optimized condition was at reaction temperature of 450°C, reaction pressure of 3.0 MPa, oil velocity of 0.1 mL/min and the gas velocity of 35 mL/min, respectively. The alkanes and alkenes content of liquid products are 50.02% and 40.03% under the optimized condition. The main products are the hydrocarbon compounds under C 18 . The results of GC online and trace water determination showed that the main products of oxygen in the oil are CO and CO 2 , and that the minor product is H 2 O. The importance and the economical production of the Non-ester renewable diesel from vegetable oil are presented. From the results of FT-IR，SF-3 and GC-MS, the generating mechanism of Non-ester renewable diesel was deduced.

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Nucleobase Protection of Deoxyribo‐ and Ribonucleosides

Cited by 10 publications

References 295 publications

Electrophilic oligodeoxynucleotide synthesis using dM-Dmoc for amino protection

Electrophilic oligodeoxynucleotide synthesis using dM-Dmoc for amino protection

Incorporation of Sensitive Ester and Chloropurine Groups into Oligodeoxynucleotides through Solid‐Phase Synthesis

PRODUCTION OF NON-ESTER RENEWABLE DIESEL BY THE HYDROGENATION OF VEGETABLE OIL ON THE 15Co5Ni-10Ce / Al2O3 CATALYST

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