NMR spectroscopy in the structural elucidation of oligosaccharides and glycosides.

Traditional cancer chemotherapy is often accompanied by systemic toxicity to the patient. Monoclonal antibodies against antigens on cancer cells offer an alternative tumor-selective treatment approach. However, most monoclonal antibodies are not sufficiently potent to be therapeutically active on their own. Antibody-drug conjugates (ADCs) use antibodies to deliver a potent cytotoxic compound selectively to tumor cells, thus improving the therapeutic index of chemotherapeutic agents. The recent approval of two ADCs, brentuximab vedotin and ado-trastuzumab emtansine, for cancer treatment has spurred tremendous research interest in this field. This Review touches upon the early efforts in the field, and describes how the lessons learned from the first-generation ADCs have led to improvements in every aspect of this technology, i.e., the antibody, the cytotoxic compound, and the linker connecting them, leading to the current successes. The design of ADCs currently in clinical development, and results from mechanistic studies and preclinical and clinical evaluation are discussed. Emerging technologies that seek to further advance this exciting area of research are also discussed.

Antibody-drug conjugates: an emerging concept in cancer therapy

Acylated anthocyanins from edible sources and their applications in food systems

Stereochemical Control in Organic-Synthesis Using Silicon-Containing Compounds

Polyphenols in foods are more complex than often thought.

In 1913 Willstatter made the striking observation that the same pigment can give rise to different colors. Thus, the same pigment, cyanin, is found in the blue cornflower and in the red rose. Willstatter attributed the variety of flower colors to different pH values in solution. Indeed, anthocyanin changes its color with pH; it appears red in acidic, violet in neutral, and blue in basic aqueous solution. Willstatter's pH-theory for explaining flower color variation is still to be found in major text books of organic chemistry. Very recently, however, reinvestigation has disclosed that the color variation and stabilization of anthocyanins in aqueous solution could have other causes, namely self-association, copigmentation and intramolecular sandwich-type stacking. The stacking would be mainly brought about by intermolecular or intramolecular hydrophobic interaction between aromatic nuclei such as anthocyanidins, flavones and aromatic acids. In addition, hydrogen bonds and charge transfer interactions may also be involved. The most interesting molecular complexes of anthocyanins are the metalloanthocyanins such as commelinin and protocyanin (blue cornflower pigment). These seemingly pure blue complexes each consist of six anthocyanin and six flavone molecules and two metal ions; their molecular weight is nearly 10000. A structure is proposed for commelinin.

Structure and Molecular Stacking of Anthocyanins—Flower Color Variation

Structure and Molecular Stacking of Anthocyanins - Flower Color Variation

Glycosidation of sialic acid

In the case of chemiluminescence of coelenterazine, effects of conformation rigidity of and hydrogen bonding with the emitter, coelenteramide, on the chemiluminescence efficiency have been examined with several coelenterazine analogues synthesized. Conformational rigidity has a light enhancing effect, whereas decreasing light yield was observed by hydrogen-bond formation with the emitter.

Toshio Goto

Papers

Structure and Molecular Stacking of Anthocyanins—Flower Color Variation

Structure and Molecular Stacking of Anthocyanins - Flower Color Variation

Glycosidation of sialic acid

Synthesis and chemiluminescence of coelenterazine(Oplophorus luciferin) analogues.

Synthesis of C-glycosyl compounds from 3,4,6-tri-O-acetyl-1,5-anhydro-D-arabino-hex-1-enitol and allyltrimethylsilane and bis(trimethylsilyl)acetylene