Amino Acids & Derivatives
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Amino acids are the basic building blocks of proteins. The condensation and derivatization of amino acids are related to the formation and function of proteins.
Progress in the synthesis of amino acids and their derivatives
Michelle C. Chang's group at the University of California, Berkeley reported on the biosynthesis mechanism of amino acid derivatives with terminal alkyne groups. The authors found that L-lysine can generate amino acid derivatives containing terminal alkynes through halogenation, oxidative elimination, and rearrangement reactions under the catalysis of a series of enzymes. Professor Xu Liwen’s team took advantage of the large steric hindrance of acylated silanes and the characteristics of desilication to form aldehydes, using unsaturated alkenyl acylated silanes as the equivalent of alkenals, and designed a new type of copper-catalyzed (3+2) cycloaddition reaction. After successfully establishing the optimal chiral control conditions, more than 20 high-ee-value chiral amino ester derivatives containing acylated silane functional groups were synthesized in high yield. In this way, the desilication reaction can be simply achieved to obtain aldehyde-based chiral amino acid derivatives, which greatly expands the functional diversity of the traditional 1,3-dipole cycloaddition reaction and solved the synthesis problem of aldehyde-containing chiral pyrrolidine (proline analog).
Application of amino acids and their derivatives
Food and feed additives: Tryptophan is an essential amino acid that plays an important biological role. Tryptophan catabolism is a signal factor that influences the host microorganism and the intestinal microbial colony. Researchers such as Wang Liqun used probiotics to regulate tryptophan metabolism, the composition of the intestinal flora was changed, and its impact on related diseases was explained, which provided new ideas for the pathogenesis and clinical treatment of related diseases.
Medicine: Molnár et al. proved that metatyrosine and o-tyrosine are potential markers of oxidative stress-related acute diseases, and may also interfere with the secretion of insulin in patients with sepsis. Hase et al. found that tyrosine can counteract the decrease in working memory, slow down information processing, and emotional deterioration that may be caused by physical or mental needs.
Biomaterials: In the design of many biomaterials, a useful method is tyrosine crosslinking. Tyrosine has many functions in natural systems, such as cross-linking of dityrosine, induction of assembly of tyrosine residues, and the role of photosystems. Curran et al. reported a new light-activated mussel protein-based bioadhesive (LAMBA), which was inspired by the adhesion of mussels and the bistyrosine cross-linking chemistry of insects.
References
- Wang LQ, Pang RC, Hu XM, Ye JM, Zhang A. Research progress on the influence of intestinal flora on tryptophan metabolism [J].Chinese Journal of Comparative Medicine, 2021, 31(04):129-136.
- Molnár G.A., Kun S., Sélley E., et al. Role of Tyrosine Isomers in Acute and Chronic Diseases Leading to Oxidative Stress-A Review[J]. Current Medicinal Chemistry, 2016, 23(7):667-685.
- Hase A., Jung S.E., Rot M. Behavioral and cognitive effects of tyrosine intake in healthy human adults [J]. Pharmacology, Biochemistry and Behavior, 2015(133):1-6.
- Jeon E.Y, Hwang B.H, Yang Y J, et al. Rapidly light-activated surgical protein glue inspired by mussel adhesion and insect structural crosslinking[J]. Biomaterials, 2015(67):11-19.
