Über neue organische Phosphorverbindungen III. Phosphinmethylenderivate und Phosphinimine

In 1919 the German chemist Hermann Staudinger was the first to describe the reaction between an azide and a phosphine. It was not until recently, however, that Bertozzi and co-workers recognized the potential of this reaction as a method for bioconjugation and transformed it into the so-called Staudinger ligation. The bio-orthogonal character of both the azide and the phosphine functions has resulted in the Staudinger ligation finding numerous applications in various complex biological systems. For example, the Staudinger ligation has been utilized to label glycans, lipids, DNA, and proteins. Moreover, the Staudinger ligation has been used as a synthetic method to construct glycopeptides, microarrays, and functional biopolymers. In the emerging field of bio-orthogonal ligation strategies, the Staudinger ligation has set a high standard to which most of the new techniques are often compared. This Review summarizes recent developments and new applications of the Staudinger ligation.

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“…[14] In the presence of water this intermediate is hydrolyzed to produce a primary amine 3 and triphenylphosphine oxide (TPPO, 4; Scheme 2).…”

Section: Staudinger Reactionmentioning

confidence: 99%

Staudinger Ligation as a Method for Bioconjugation

2011

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“…Generally, problems arising from heterogenic phase hydrogenation can be overcome by reducing the azido group of a pentofuranuronic building block with tertiary phosphines under well-established conditions of the Staudinger reaction (Staudinger and Meyer 1919;Staudinger and Hauser 1921;Leffler and Temple 1967;Gololobov et al 1981;Gololobov 1992;Simone et al 2005;Brase et al 2005;Van Rompaey et al 2005;Temelkoff et al 2006): a method introduced for azidosugars as early as 1964 (Messmer et al 1964). The applicability of the Staudinger reaction in peptide chemistry was confirmed in the early 2000s (Saxon et al 2000;Nilsson et al 2000), and its applicability to solid phase synthesis was shown in the same year (Malkinson et al 2000;Lundquist and Pelletier 2001).…”

Section: Introductionmentioning

confidence: 99%

Origin of problems related to Staudinger reduction in carbopeptoid syntheses

et al. 2016

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We report the solid phase synthesis of -GG-X-GG-type α/β-carbopeptoids incorporating RibAFU(ip) (1a, tX) or XylAFU(ip) (2a, cX) sugar amino acids. Though coupling efficacy is moderate, both the lengthier synthetic route using Fmoc deriva-tive (e.g., Fmoc-RibAFU(ip)-OH) and the azido deriva-tive (e.g., N 3 -RibAFU(ip)-OH) via Staudinger reaction with nBu 3 P can be successfully applied. Both X-ray dif-fraction, 1 H-and 31 P-NMR, and theoretical (QM) data support and explain why the application of Ph 3 P as Staudinger reagent is "ineffective" in the case of a cis stereoisomer, if cX is attached to the preceding residue with a peptide (-CONH-) bond. The failure of the poly-peptide chain elongation with N 3 -cX originates from the "coincidence" of a steric crowdedness and an electronic effect disabling the mandatory nucleophilic attack dur-ing the hydrolysis of a quasi penta-coordinated triph-enylphosphinimine. Nevertheless, the synthesis of the above α/β-chimera peptides as completed now by a new pathway via 1,2-O-isopropylidene-3-azido-3-deoxy-ribo-and -xylo-furanuronic acid (H-RibAFU(ip)-OH 1a and H-XylAFU(ip)-OH 2a) coupled with N-protected α-amino acids on solid phase could serve as useful examples and starting points of further synthetic efforts.

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“…The azido-alcohols 7 and 8 were used in the synthesis of the azido-ethers 9-14 by phase-transfer catalyzed alkylations, which, except for 12, were reduced under hydrogenation conditions in presence of Pd/C to afford the corresponding diamine derivative 15-20 in 74-95% yield. Chemoselective reduction of compound 12 was achieved following the method described by Staudinger, Meyer (1919), using triphenylphosphine. The platinum complexes 1-6 were synthesized by reaction of equimolar amount of the appropriate diamine with K 2 PtCl 4 , in 12-55% (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

Synthesis and evaluation of platinum complexes with potential antitumor activity

Freire

Marques

Souza-Fagundes

et al. 2017

Braz. J. Pharm. Sci.

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A novel series of platinum (II) complexes was synthesized and the complexes were evaluated for their in vitro cytotoxicity against four human cancer cells lines. Five platinum complexes showed activity against at least one tumor cell line. Complexes 3 and 6 were promising, being active, at micromolar concentrations, against all the assayed tumor cell lines. Compound 3 was selected for further studies in mice with Ehrlich solid tumors and it was able to reduce the rate of tumor growth significantly during the first seven days. However, at the end of the experiments, there was no significant difference between the group of animals treated with 3 and the control group. The low solubility of the compound in the assay conditions can explain, at least in part, these results.Uniterms:. /Cytotoxic activity. Platinum complexes/ Ehrlich solid tumor activity.

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Über neue organische Phosphorverbindungen III. Phosphinmethylenderivate und Phosphinimine

Abstract: Benzoyldiazoessigester reagiert ebenfalls rnit beiclen Phosphineri. Die erhaltenen Azine werden spater beschrieben.

Cited by 1,442 publications

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Staudinger Ligation as a Method for Bioconjugation

Staudinger Ligation as a Method for Bioconjugation

Origin of problems related to Staudinger reduction in carbopeptoid syntheses

Synthesis and evaluation of platinum complexes with potential antitumor activity

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