Synthesis of 3,4,5-trisubstituted isoxazoles in water via a [3 + 2]-cycloaddition of nitrile oxides and 1,3-diketones, β-ketoesters, or β-ketoamides

• Md Imran Hossain,
• Md Imdadul H. Khan,
• Seong Jong Kim and
• Hoang V. Le

Beilstein J. Org. Chem. 2022, 18, 446–458, doi:10.3762/bjoc.18.47

• oxide and strained alkenes has been used to achieve the high-density functionalization of oligodeoxyribonucleotides [29]. However, the alkenes need to be highly strained in order for this reaction to occur without the need for an additional metal catalyst. As an alternative to the mild acidic conditions

Double-headed nucleosides: Synthesis and applications

• Vineet Verma,
• Jyotirmoy Maity,
• Vipin K. Maikhuri,
• Ritika Sharma,
• Himal K. Ganguly and
• Ashok K. Prasad

Beilstein J. Org. Chem. 2021, 17, 1392–1439, doi:10.3762/bjoc.17.98

• nucleoside monomers 125a–c were incorporated into oligodeoxyribonucleotides via phosphoramidite derivatization of the C-3′ hydroxy group present in the moiety. The oligonucleotides thus synthesized were found to stabilize the duplex formed with complementary DNA [69]. Nielsen and co-workers [43][70

Synthesis of 10-O-aryl-substituted berberine derivatives by Chan–Evans–Lam coupling and investigation of their DNA-binding properties

• Peter Jonas Wickhorst,
• Mathilda Blachnik,
• Denisa Lagumdzija and
• Heiko Ihmels

Beilstein J. Org. Chem. 2021, 17, 991–1000, doi:10.3762/bjoc.17.81

• buffer solution. Oligodeoxyribonucleotides (HPLC purified) d[A(GGGTAA)3GGG] (22AG), F21T [fluo-G3(TTAG3)3-tamra; fluo = fluorescein, tamra = tetramethylrhodamine], Fa2T [fluo-(ACAG3TGT)2-tamra], FmycT [fluo-TGAG3TG3TAG3TG3TA-tamra] and FkitT [fluo-AG3AG3CGCTG3AG2AG3-tamra] were purchased from Biomers.net

Synthesis of oligonucleotides on a soluble support

• Harri Lönnberg

Beilstein J. Org. Chem. 2017, 13, 1368–1387, doi:10.3762/bjoc.13.134

• Scheme 1). Compared to oligodeoxyribonucleotides (ODNs), the synthesis of oligoribonucleotides (ORNs) is complicated by the presence of an additional nucleophilic functionality, viz. the 2´-OH that has to be kept protected as long as basic conditions are required during synthesis and deprotection of the

• , impressive examples of classical convergent synthesis [31][32][33][34] and exploitation of solid-supported reagents in solution [35][36] have been reported. The present review, however, surveys only the progress of ON synthesis on a soluble support. Review Synthesis of oligodeoxyribonucleotides by

• related reductively cleavable disulfide-linked support 7 [50]. Synthesis of oligodeoxyribonucleotides by phosphoramidite chemistry As mentioned above, phosphoramidite chemistry is nowadays the method of choice for the solid-supported synthesis of oligonucleotides both in small and large scale. The first

Preparation of a disulfide-linked precipitative soluble support for solution-phase synthesis of trimeric oligodeoxyribonucleotide 3´-(2-chlorophenylphosphate) building blocks

• Amit M. Jabgunde,
• Alejandro Gimenez Molina,
• Pasi Virta and
• Harri Lönnberg

Beilstein J. Org. Chem. 2015, 11, 1553–1560, doi:10.3762/bjoc.11.171

• -protected oligodeoxyribonucleotide trimer 3’-pTpdCBzpdGibu-5’ as its 3’-(2-chlorophenyl phosphate) was achieved by reductive cleavage of the disulfide bond. Keywords: disulfide linker; oligodeoxyribonucleotides; phosphotriester chemistry; precipitation; soluble support; Introduction Synthetic nucleic

A comparative study of the interactions of cationic hetarenes with quadruplex-DNA forming oligonucleotide sequences of the insulin-linked polymorphic region (ILPR)

• Darinka Dzubiel,
• Heiko Ihmels,
• Mohamed M. A. Mahmoud and
• Laura Thomas

Beilstein J. Org. Chem. 2014, 10, 2963–2974, doi:10.3762/bjoc.10.314

• Organics, Geel, Belgium; 4, 6: Fluka Chemie AG, Buchs, Switzerland). The [2.2.2]heptamethine cyanine dyes 1a–e [22], bis-quinolinium 3 [39] and tetraazoniahetarene 5 [23] were synthesized according to published procedures. Oligodeoxyribonucleotides (HPLC purified) a2 [d(ACAG4TGTG4ACAG4TGTG4)] and Fa2T [d

Solution phase synthesis of short oligoribonucleotides on a precipitative tetrapodal support

• Alejandro Gimenez Molina,
• Amit M. Jabgunde,
• Pasi Virta and
• Harri Lönnberg

Beilstein J. Org. Chem. 2014, 10, 2279–2285, doi:10.3762/bjoc.10.237

• them has so far been applied to the synthesis of RNA. Tetrakis(4-azidomethylphenyl)pentaerythritol has recently been introduced as a practical soluble support for the synthesis of short oligodeoxyribonucleotides [16]. The 3'-terminal nucleoside is attached as a 3'-O-(4-pentynoyl) derivative to the