Polyamide based nucleic acid analogs — synthesis of δ-amino acids with nucleic acid bases bearing side chains

Altmann, Karl‐Heinz; Chiesi, Chantal Schmit; García‐Echeverría, Carlos

doi:10.1016/s0960-894x(97)00172-8

Cited by 18 publications

(6 citation statements)

References 26 publications

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“… N 4 -Benzoyl cytosine has a poor solubility in THF/dioxane, and the reaction may not work well. Cytosine derivatives could be prepared via uracil to cytosine base conversion For guanine-based nonsugar nucleosides, use of O -carbamate- N -acetate protected guanine as the nucleophile in THF at 70 °C with Ph 3 P−DIAD added twice, 1 equiv each time, provided the best yields .…”

Section: Amines Amides (Including Nucleobases) or Azides As Nucleophilesmentioning

confidence: 99%

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Mitsunobu and Related Reactions: Advances and Applications

et al. 2009

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His research interests include Organophosphorus Chemistry and Main Group Chemistry. He has over 115 publications so far and is a fellow of the Indian Academy of Sciences, Bangalore. N. N. Bhuvan Kumar was born in Cherukupalli, Guntur, India. After completing his B.Sc. from Nagarjuna University, he joined the School of Chemistry, University of Hyderabad, as a postgraduate student in the year 2000 and obtained his Master's degree in Chemistry. Currently, he is pursuing a Ph.D. on Organophosphonates under the supervision of Prof. K. C. Kumara Swamy. E. Balaraman was born in Kancheepuram, Chennai, India, in 1980. He received his M.Sc. in Chemistry from Vivekananda College [Madras University (2002)] and his Ph.D. degree in the areas of organophosphonates and modified BINOLs under the guidance of Prof. K. C. Kumara Swamy. Presently he is a postdoctoral fellow with Professors David Milstein and Ronny Neumann at the Weizmann Institute of Science, Israel. K. V. P. Pavan Kumar was born in Hyderabad (Andhra Pradesh), India, in 1979. He obtained his B.Sc. (Chemistry Honors) and M.Sc. (Chemistry) degrees from Sri Sathya Sai Institute of Higher Learning, Puttaparthi, A.P., India. He obtained his Ph.D. degree under the guidance of Prof. K. C. Kumara Swamy in October 2006. Presently he is working as a postdoctoral fellow in the area of hydroamination reactions using new titanium catalysts with Prof. Pierre Le Gendre at the Universite ´de Bourgogne, France.

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Section: Amines Amides (Including Nucleobases) or Azides As Nucleophilesmentioning

confidence: 99%

“…N 4 -Benzoyl cytosine has a poor solubility in THF/dioxane, and the reaction may not work well. Cytosine derivatives could be prepared via uracil to cytosine base conversion …”

Section: Amines Amides (Including Nucleobases) or Azides As Nucleophilesmentioning

confidence: 99%

Mitsunobu and Related Reactions: Advances and Applications

et al. 2009

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“…Pseudodipeptide derivatives 17 and 18 were synthesized by similar procedures (Scheme 4). However, for the synthesis of tert -butyl ester derivative the reaction of Z-L-norleucinol with tert -butyl bromoacetate was carried out under phase transfer conditions 33,34…”

Section: Resultsmentioning

confidence: 99%

2-Oxoamide inhibitors of phospholipase A2 activity and cellular arachidonate release based on dipeptides and pseudodipeptides

Barbayianni

Stephens²,

Grkovich³

et al. 2009

Bioorganic & Medicinal Chemistry

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A series of 2-oxoamides based on dipeptides and pseudodipeptides were synthesized and their activities toward two human intracellular phospholipases A 2 (GIVA cPLA 2 and GVIA iPLA 2 ) and one human secretory phospholipase A 2 (GV sPLA 2 ) were evaluated. Derivatives containing a free carboxyl group are selective GIVA cPLA 2 inhibitors. A derivative based on the ethyl ester of an ether pseudodipeptide is the first 2-oxoamide, which preferentially inhibits GVIA iPLA 2 . The effect of 2-oxoamides on the generation of arachidonic acid from RAW 264.7 macrophages was also studied and it was found that selective GIVA cPLA 2 inhibitors preferentially inhibited cellular arachidonic acid release; one pseudodipeptide gave an IC 50 value of 2 μM.

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“…They are found as pyranoid δ-SAA with the amino group often functionalised with acetyl or glycosyl groups, and are important component of cell surface glycoconjugates involved in cellular recognition processes. Moreover, the same authors synthesised on solid-phase linear oligomers of a neuraminic acid derivative using Fmoc-NeuAc (101). Gervay et al reported the synthesis of Boc-amino-and carboxy-protected derivatives of NeuAc, of the corresponding amide-linked homodimers [51], and the conjugation of N-acetyl neuraminic acid with α-amino acids in solution [52].…”

Section: Sugar Amino Acidsmentioning

confidence: 99%

γ- and δ-Amino Acids: Synthetic Strategies and Relevant Applications

Trabocchi¹,

Guarna

2005

COC

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Over the years, γand δ-amino acids have gathered much interest in drug discovery, especially in the peptidomimetic area. Much work on γ-amino acids has been focused towards the generation of γ-amino butyric acid (GABA) analogues, and the development of asymmetric approaches starting from unsaturated compounds, while few examples have been reported about carbohydrate-derived scaffolds as γ-amino acids. δ-Amino acids became of great importance as they have been selected as building blocks for backbone generation of peptide nucleic acid (PNA) structures. As further applications of δ-amino acids, carbohydrate research produced interesting examples of new δ-amino acids as building blocks for peptidomimetic design, and several reverse turn mimetics have been reported, too. Moreover, many studies have been concentrated on the conformational analysis of oligomeric sequences in analogy with β-peptides. This report is a description of relevant synthetic approaches to new γ-amino acids through the use of sugar chemistry and asymmetric synthesis, and to synthetic strategies for δ-amino acids, covering the area of carbohydrate chemistry, alkenebased chemistry, and asymmetric synthesis. 10γ -and δ -Amino Acids: Synthetic Strategies

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Polyamide based nucleic acid analogs — synthesis of δ-amino acids with nucleic acid bases bearing side chains

Cited by 18 publications

References 26 publications

Mitsunobu and Related Reactions: Advances and Applications

Mitsunobu and Related Reactions: Advances and Applications

2-Oxoamide inhibitors of phospholipase A2 activity and cellular arachidonate release based on dipeptides and pseudodipeptides

γ- and δ-Amino Acids: Synthetic Strategies and Relevant Applications

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Polyamide based nucleic acid analogs — synthesis of δ-amino acids with nucleic acid bases bearing side chains

Cited by 18 publications

References 26 publications

Mitsunobu and Related Reactions: Advances and Applications

Mitsunobu and Related Reactions: Advances and Applications

2-Oxoamide inhibitors of phospholipase A2 activity and cellular arachidonate release based on dipeptides and pseudodipeptides

&#947;- and &#948;-Amino Acids: Synthetic Strategies and Relevant Applications

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γ- and δ-Amino Acids: Synthetic Strategies and Relevant Applications