Einfache Herstellung von <i>N</i>‐Acyl‐2‐(diethoxyphosphoryl)‐glycinestern und ihre Verwendung zum Aufbau von Dehydroaminosäureestern

Schmidt, Ulrich; Lieberknecht, Albrecht; Schanbacher, Ute; Beuttler, Thomas; Wild, Jochen

doi:10.1002/ange.19820941027

Cited by 30 publications

(2 citation statements)

References 3 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…With respect to their limited stability, thymidine-5'-aldehydes 10 and 11 were not stored, but directly used for the subsequent Wittig–Horner reaction. They were therefore converted with glycine-derived phosphonate 12 [ 51 – 54 ] in the presence of potassium tert -butoxide as a base. As anticipated [ 47 – 48 55 ], these reactions showed pronounced stereoselectivity towards the Z -configured didehydro nucleosyl amino acids.…”

Section: Resultsmentioning

confidence: 99%

NAA-modified DNA oligonucleotides with zwitterionic backbones: stereoselective synthesis of A–T phosphoramidite building blocks

Schmidtgall¹,

Höbartner²,

Ducho³

2015

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

SummaryModifications of the nucleic acid backbone are essential for the development of oligonucleotide-derived bioactive agents. The NAA-modification represents a novel artificial internucleotide linkage which enables the site-specific introduction of positive charges into the otherwise polyanionic backbone of DNA oligonucleotides. Following initial studies with the introduction of the NAA-linkage at T–T sites, it is now envisioned to prepare NAA-modified oligonucleotides bearing the modification at X–T motifs (X = A, C, G). We have therefore developed the efficient and stereoselective synthesis of NAA-linked 'dimeric' A–T phosphoramidite building blocks for automated DNA synthesis. Both the (S)- and the (R)-configured NAA-motifs were constructed with high diastereoselectivities to furnish two different phosphoramidite reagents, which were employed for the solid phase-supported automated synthesis of two NAA-modified DNA oligonucleotides. This represents a significant step to further establish the NAA-linkage as a useful addition to the existing 'toolbox' of backbone modifications for the design of bioactive oligonucleotide analogues.

show abstract

Section: Resultsmentioning

confidence: 99%

NAA-modified DNA oligonucleotides with zwitterionic backbones: stereoselective synthesis of A–T phosphoramidite building blocks

Schmidtgall¹,

Höbartner²,

Ducho³

2015

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

show abstract

“…In general, the (Z)-isomer is the major product (Scheme 9). Schmidt and co-workers used phosphoranes obtained from the a-hydroxyglycine esters via a-phosphoryl esters 20 [17], and the N-[(benzyloxy)-carbonyl]-protected methyl ester of glycine is commercially available.…”

Section: Scheme 4 Schemementioning

confidence: 99%

Expanding the Genetic Alphabet: Pyrazine Nucleosides That Support a DonorDonorAcceptor Hydrogen‐Bonding Pattern

Krosigk

Benner

2004

Helvetica Chimica Acta

View full text Add to dashboard Cite

The 6-aminopyrazin-2(1H)-one, when incorporated as a pyrimidine-base analog into an oligonucleotide chain, presents a H-bond donorÀdonorÀacceptor pattern to a complementary DNA or RNA strand. When paired with the corresponding acceptorÀacceptorÀdonor purine in oligonucleotides, the heterocycle selectively contributes to the stability of the duplex, presumably by forming a base pair of WatsonÀCrick geometry joined by a nonstandard H-bonding pattern, expanding the genetic alphabet. Reported here is a short, high yielding, bd-selective synthesis of a 6-aminopyrazin-2(1H)-one nucleoside via the glycine riboside derivative 28. The key steps include a WittigÀHorner reaction of an appropriately protected ribose derivative (Scheme 10, 19 3 21) followed by a Michael-like ring closure (Scheme 12, 30 3 1a and 32 3 1b). Thus, a variety of pyrazine nucleosides (Scheme 13) including the target 6-aminopyrazin-2(1H)-one riboside 1a, and its 5-methyl derivative 1b, 6-amino-5-methylpyrazin-2(1H)-one riboside, are obtained.

show abstract

Unusual amino acids VI. Substituted arylamino acids by asymmetric hydrogenation ofN-Cbz andN-Boc protected dehydroamino acid derivatives

et al. 1996

View full text Add to dashboard Cite

Einfache Herstellung von N‐Acyl‐2‐(diethoxyphosphoryl)‐glycinestern und ihre Verwendung zum Aufbau von Dehydroaminosäureestern

Cited by 30 publications

References 3 publications

NAA-modified DNA oligonucleotides with zwitterionic backbones: stereoselective synthesis of A–T phosphoramidite building blocks

NAA-modified DNA oligonucleotides with zwitterionic backbones: stereoselective synthesis of A–T phosphoramidite building blocks

Expanding the Genetic Alphabet: Pyrazine Nucleosides That Support a DonorDonorAcceptor Hydrogen‐Bonding Pattern

Unusual amino acids VI. Substituted arylamino acids by asymmetric hydrogenation ofN-Cbz andN-Boc protected dehydroamino acid derivatives

Contact Info

Product

Resources

About