Unnatural Base Pairs for Synthetic Biology

Saito–Tarashima, Noriko; Minakawa, Noriaki

doi:10.1248/cpb.c17-00685

Cited by 15 publications

(11 citation statements)

References 47 publications

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“…Modified or completely artificial base moieties can imbue oligonucleotides with new properties, such as alternative base pairing patterns, [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16] catalytic activity 17,18 or the ability to bind metal ions, either coordinatively [19][20][21][22][23][24] or through formation of a carbon-metal bond. 25,26 Unnatural base moieties are most commonly introduced into oligonucleotides as phosphoramidite building blocks of the corresponding nucleoside analogues by automated solid-phase synthesis.…”

Section: Introductionmentioning

confidence: 99%

N-Methoxy-1,3-oxazinane nucleic acids (MOANAs) – a configurationally flexible backbone modification allows post-synthetic incorporation of base moieties

2022

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Section: Introductionmentioning

confidence: 99%

N-Methoxy-1,3-oxazinane nucleic acids (MOANAs) – a configurationally flexible backbone modification allows post-synthetic incorporation of base moieties

2022

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“…The concept of non-standard nucleotide gained its popularity over the last few years. The non-standard nucleotides were chemically designed in such a manner that the complementary base pairs are highly specific and selective in nature (Malyshev et al, 2014;Saito-Tarashima et al, 2018).…”

Section: Fundamentals On Dna and Its Molecular Structurementioning

confidence: 99%

Extended nucleic acid memory as the future of data storage technology

Biswas¹,

Nath²,

Sing³

et al. 2020

IJNBM

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The amount of operational data being generated at an exponential rate in various spheres of computing, in turn, has culminated in a pressure on the available silicon memory-constrained by its limited capacity. In recent times, research has been undertaken on DNA computing for memory technology where nucleic acid memory (NAM) was formulated and found to be an efficient alternative for storing a large amount of digital data in the molecular space. This work presents a new encoding scheme which efficiently maps the binary data into a hybrid system of standard as well as non-standard genetic nucleotides to achieve a higher data capacity. Comparative studies have been done with existing encoding schemes, moreover, this work demonstrates the use of unnatural base pairs like Ds-Px and Im-Na which exhibit high stability and high selectivity in a DNA molecule.

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“…Myriad artificial nucleobase analogues have been incorporated into oligonucleotides and tested for their potential to stabilize double helices through enhanced stacking, [1][2][3][4][5] hydrogen bonding [6][7][8][9][10][11][12][13][14] or shape complementarity, [15][16][17] to expand the genetic alphabet [18][19][20][21][22][23] and to serve as specific high-affinity binding sites for metal ions. [24][25][26][27][28][29] A strategy to introduce base moieties post-synthetically to a common scaffold, preferably under aqueous conditions, would greatly facilitate such studies.…”

Section: Introductionmentioning

confidence: 99%

Improved Synthesis Strategy for N‐Methoxy‐1,3‐oxazinane Nucleic Acids (MOANAs)

Wallin

Lönnberg

2022

Eur J Org Chem

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Dependence of the hydrolysis rate of a series of N-methoxy-2phenyl-1,3-oxazinanes on the Hammett substituent constant of the substituent of the phenyl ring was determined, yielding a reaction constant 1 = À 1.40 � 0.05. Based on this information, 4-(benzoyloxy)benzaldehyde was selected as a protecting group for a new (2R,3S)-4-(methoxyamino)butane-1,2,3-triol phosphoramidite building block. The yield of the preparation of this building block as well as its coupling in automated oligonucleotide synthesis were greatly improved compared to the method reported previously. The 2-[4-(benzoyloxy)phenyl]-1,3-oxazine protection persisted throughout the synthesis of short oligonucleotides but was rapidly removed when the oligonucleotides were released from solid support and dissolved in water.

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Unnatural Base Pairs for Synthetic Biology

Cited by 15 publications

References 47 publications

N-Methoxy-1,3-oxazinane nucleic acids (MOANAs) – a configurationally flexible backbone modification allows post-synthetic incorporation of base moieties

N-Methoxy-1,3-oxazinane nucleic acids (MOANAs) – a configurationally flexible backbone modification allows post-synthetic incorporation of base moieties

Extended nucleic acid memory as the future of data storage technology

Improved Synthesis Strategy for N‐Methoxy‐1,3‐oxazinane Nucleic Acids (MOANAs)

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