Syntheses of racemic and non-racemic silicon- and germanium-containing α-amino acids of the formula type H2NCH(CH2ElR3)COOH (El=Si, Ge; R=organyl) and incorporation of d-H2NCH(CH2SiMe3)COOH and d-H2NCH(CH2GeMe3)COOH into biologically active decapeptides: a study on C/Si/Ge bioisosterism

Merget, Markus; Günther, Kurt; Bernd, Michael; Günther, E; Tacke, Reinhold

doi:10.1016/s0022-328x(01)00783-5

Cited by 47 publications

(19 citation statements)

References 25 publications

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“…UV and fluorescence spectra were recorded with a Perkin Elmer LS 50 spectrometer. Monobenzyl succinate 5 7 and the following amino acid derivatives were prepared according to reported protocols: N ‐Fmoc‐β‐Ala,8 N ‐Fmoc‐ L ‐Pro,9 N ‐Fmoc‐ L ‐Npg,10 N ‐Boc‐β‐Ala,11 N ‐Boc‐ L ‐Val,12 β‐Ala‐O t Bu,13 L ‐Npg‐OMe,14 and Aib–OMe 15. All other starting materials were commercially available.…”

Section: Methodsmentioning

confidence: 99%

Diaminoterephthalates: Scaffolds for Combinatorial Chemistry

Pflantz

Christoffers

2009

Chemistry A European J

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Fluorescent building blocks: Tetracarboxyamides with a central fluorescent diaminoterephthalate unit were prepared from succinyl succinates following a combinatorial-like strategy. The 2,5-diaminoterephthalates (see scheme; PG=protecting group) possess four points of diversification and are introduced as new scaffolds for combinatorial chemistry.2,5-Diaminoterephthalates that possess four points of diversification are introduced as new scaffolds for combinatorial chemistry. A straightforward synthesis of an orthogonally protected platform compound was developed. This platform was transformed by stepwise deprotection and amidation of the two amino and two carboxylic acid moieties into tetra-amides with a central aromatic ring as a fluorescence chromophore.

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Section: Methodsmentioning

confidence: 99%

Diaminoterephthalates: Scaffolds for Combinatorial Chemistry

Pflantz

Christoffers

2009

Chemistry A European J

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“…β-Silylation of dihydropyrazine 44 affords the racemic mixture of TMSAla 38a and two derivatives 38b and 38g (Scheme ). This synthesis was performed in three or four steps from dihydropyrazine 44 by metalation with n- butyllithium and monoalkylation with a silicon-containing derivative, affording a mixture of 45 and unreactive dehydropyrazine 44 . After treatment under acidic conditions, the β-silyl α-amino esters 38d – f were isolated and hydrolyzed to afford the corresponding free amino acids in overall yields of 42% ( 38a ), 21% ( 38b ), and 12% ( 38g ).…”

Section: β-Silyl α-Amino Acidsmentioning

confidence: 99%

Silicon-Containing Amino Acids: Synthetic Aspects, Conformational Studies, and Applications to Bioactive Peptides

et al. 2016

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Unnatural α-amino acids form a family of essential molecules used for, among other applications, the synthesis of modified peptides, to improve resistance to proteolytic enzyme degradation, and to modulate physico- and biochemical properties of bioactive peptides as well as chiral inducers in asymmetric synthesis. Among them, silicon-containing unnatural amino acids are becoming an interesting new class of building blocks. The replacement of carbon atoms in bioactive substances with silicon is becoming increasingly popular. Peptides containing silyl amino acids hold great promise for maintaining or reinforcing the biological activity of active compounds, while they simultaneously enhance their resistance to enzyme degradation. In addition, the lipophilicity of the silicon atom facilitates their membrane crossing and their bioavailability. Nowadays, the interest of the pharmaceutical industry in peptide- and protein-based therapies is increasing. In this respect, silicon-containing amino acids and peptides are likely to be a significant part of future innovations in this area, and more generally in the area of biomolecules. In this process, commercial availability of silicon-containing amino acids is necessary: new syntheses have been developed, and work in this area is ongoing. This review aims to be a comprehensive and general summary of the different methods used to prepare silicon-containing amino acids and their implications on conformational structures and biological applications when they are incorporated into bioactive molecules.

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“…Germanium containing α-aminoacids and peptides and their incorporation into biologically active decapeptides has been reported 22,23. The 6-trialkylgermyl-5-fluorouridine derivatives are one of the few known examples of germanium-containing nucleoside analogues24 and 5-trimethylgermyl-2′-deoxyuridine was showed to inhibit HSV-1 replication in vitro and blocked incorporation of thymidine into DNA of cancer ovarian cells 25.…”

Section: Introductionmentioning

confidence: 99%

Application of Germyldesulfonylation Reactions to the Synthesis of Germanium-Containing Nucleoside Analogues

Wnuk

Sacasa

Restrepo

2009

Nucleosides, Nucleotides & Nucleic Acids

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Treatment of the protected (E)-5′-deoxy-5′- [(p-toluenesulfonyl)methylene]uridine and adenosine derivatives with tributyl-or triphenylgermane hydride (AIBN/toluene/Δ) effected radical-mediated germyldesulfonylations to give 5′-(tributyl-or triphenylgermyl)methylene-5′-deoxyuridine and adenosine derivatives as single (E)-isomers. Analogous treatment of 2′-deoxy-2′-[(phenylsulfonyl) methylene]uridine with Ph 3 GeH afforded the corresponding vinyl triphenylgermane product. Stereoselective halodegermylation of the (E)-5′-(tributylgermyl)methylene-5′-deoxy nucleosides with N-iodosuccinimide or N-bromosuccinimide provided the Wittig-type (E)-5′-deoxy-5′-(halomethylene) nucleosides quantitatively, while no halodegermylations was observed with the 5′-deoxy-5′-(triphenylgermyl)methylene counterparts. Treatment of the vinyl trialkylgermanes with aqueous trifluoroacetic acid effected protiodegermylation, while vinyl triarylgermanes were stable under the acidic conditions.

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Syntheses of racemic and non-racemic silicon- and germanium-containing α-amino acids of the formula type H2NCH(CH2ElR3)COOH (El=Si, Ge; R=organyl) and incorporation of d-H2NCH(CH2SiMe3)COOH and d-H2NCH(CH2GeMe3)COOH into biologically active decapeptides: a study on C/Si/Ge bioisosterism

Cited by 47 publications

References 25 publications

Diaminoterephthalates: Scaffolds for Combinatorial Chemistry

Diaminoterephthalates: Scaffolds for Combinatorial Chemistry

Silicon-Containing Amino Acids: Synthetic Aspects, Conformational Studies, and Applications to Bioactive Peptides

Application of Germyldesulfonylation Reactions to the Synthesis of Germanium-Containing Nucleoside Analogues

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