A new hydrogen-abstracting reaction with diethyl azodicarboxylate

Yoneda, Fumio; Suzuki, Kunio; Nitta, Yoshihiro

doi:10.1021/jo01278a049

Cited by 71 publications

(17 citation statements)

References 3 publications

(7 reference statements)

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“…Further experiments performed on (R)-4h and racemic 4h showed that 7h was formed also in the absence of phthalimide. DEAD is able to oxidise alcohols to ketones, 35,36 but in this case a reaction using only DEAD failed to give 7h. Thus, both DEAD and triphenylphosphine were required for the transformation.…”

Section: Tablementioning

confidence: 95%

Enantioenriched 1-aryl-2-fluoroethylamines. Efficient lipase-catalysed resolution and limitations to the Mitsunobu inversion protocol

Thvedt

Fuglseth

Sundby³

et al. 2010

Tetrahedron

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Section: Tablementioning

confidence: 95%

Enantioenriched 1-aryl-2-fluoroethylamines. Efficient lipase-catalysed resolution and limitations to the Mitsunobu inversion protocol

Thvedt

Fuglseth

Sundby³

et al. 2010

Tetrahedron

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“…These properties also predestine the DAR inv as a suitable technology for an intravital ligation of functional components in living systems. As shown here, the synthesis of disulfide-functionalized molecules is possible by use of production techniques like the mercaptane oxidation of different hydrogen sulfide containing molecules [27][28][29]. We suggest the coupling of SH-groups of terminal cysteines by oxidation and the formation of disulfide-bridges was carried out by use of mild oxidants, but yields of the obtained disulfide-containing molecule are limited and a loss of 60% must be accepted.…”

Section: Introductionmentioning

confidence: 94%

Amide-based Disulfide Building Blocks for the Enlargement of the Solid Phase Peptide Synthesis for Molecular Diagnostics and Imaging

Braun¹,

Wießler²,

Komljenovic³

et al. 2014

Pharmaceut Reg Affairs

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Progress in genome and proteome research led to a deeper insight in differential gene expression processes. This required the use of sensitive and specific tools in diagnostics; also new promising patient-specific therapy attempts are conceivable. Nucleic acids were up till now a critical goal for diagnostic applications and therapeutic interventions, but in future they can serve as highly sequence-specific tools in molecular diagnostics. Examples for diagnostic Molecular Imaging modalities are the analysis of metabolic processes which can lead to customized therapeutic approaches ("Targeted Therapy"). The solid phase peptide synthesis SPPS is considered as an excellent tool in the individualized medicine with nucleic acids which increasingly play a key role as a drug. This requires new properties of the nucleic acid-based drugs, contiguous to the stability in biological systems, a high variability by combination with functional peptide-based molecules or with reformulated drugs or imaging components. The multifaceted application spectrum is dependent on the patients' individual differential gene expression profiles or on the medical questionnaire. Here we show a new synthesis strategy able to circumvent ligations steps and to enhance the yields in the SPPS technology by use of a novel disulfide-containing monomer. This molecule acts as a disulfide linker which can overcome the common occasional losses occurring during established coupling reactions, like disulfide-bridge formations.

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“…Technically, the functionalization of nucleic acids and their derivatives with thiol-groups for oxidative connection of functional peptides was documented 6 . The synthesis of disulfide- functionalized molecules was also described 7 - 10 .…”

Section: Introductionmentioning

confidence: 99%

NIR-Cyanine Dye Linker: a Promising Candidate for Isochronic Fluorescence Imaging in Molecular Cancer Diagnostics and Therapy Monitoring

Komljenovic¹,

Wießler²,

Waldeck³

et al. 2016

Theranostics

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Personalized anti-cancer medicine is boosted by the recent development of molecular diagnostics and molecularly targeted drugs requiring rapid and efficient ligation routes. Here, we present a novel approach to synthetize a conjugate able to act simultaneously as an imaging and as a chemotherapeutic agent by coupling functional peptides employing solid phase peptide synthesis technologies. Development and the first synthesis of a fluorescent dye with similarity in the polymethine part of the Cy7 molecule whose indolenine-N residues were substituted with a propylene linker are described. Methylating agent temozolomide is functionalized with a tetrazine as a diene component whereas Cy7-cell penetrating peptide conjugate acts as a dienophilic reaction partner for the inverse Diels-Alder click chemistry-mediated ligation route yielding a theranostic conjugate, 3-mercapto-propionic-cyclohexenyl-Cy7-bis-temozolomide-bromide-cell penetrating peptide. Synthesis route described here may facilitate targeted delivery of the therapeutic compound to achieve sufficient local concentrations at the target site or tissue. Its versatility allows a choice of adequate imaging tags applicable in e.g. PET, SPECT, CT, near-infrared imaging, and therapeutic substances including cytotoxic agents. Imaging tags and therapeutics may be simultaneously bound to the conjugate applying click chemistry. Theranostic compound presented here offers a solid basis for a further improvement of cancer management in a precise, patient-specific manner.

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A new hydrogen-abstracting reaction with diethyl azodicarboxylate

Cited by 71 publications

References 3 publications

Enantioenriched 1-aryl-2-fluoroethylamines. Efficient lipase-catalysed resolution and limitations to the Mitsunobu inversion protocol

Enantioenriched 1-aryl-2-fluoroethylamines. Efficient lipase-catalysed resolution and limitations to the Mitsunobu inversion protocol

Amide-based Disulfide Building Blocks for the Enlargement of the Solid Phase Peptide Synthesis for Molecular Diagnostics and Imaging

NIR-Cyanine Dye Linker: a Promising Candidate for Isochronic Fluorescence Imaging in Molecular Cancer Diagnostics and Therapy Monitoring

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