"Black vomit" is a serious disease for chicken, which is accompanied by gizzard erosion or ulceration. In 1983, Naito et al. investigated the cause of this disease and isolated an amino acid gizzerosine 1 as a potent inducer of gizzard erosion, which was generated during the heat treatment of brown fish meal. We synthesized 1 using two successive coupling reactions: A) Zinc-mediated coupling reaction of the serine-derived iodide with 3-bromo-1-propenyl acetate. B) Palladium-catalyzed coupling reaction with N-piperonylhistamine.


228. "Analytical Method to Evaluate Gizzerosine in Fishmeal After Diazonium Derivatization Using High-Performance Liquid Chromatography"
Zhi-Hua Tao, Qin-Xia Hu, Xiao-Jing Xu, Hiromasa Kiyota, Ze-Xi Chen, Shu-Ying Xie, Na Qiao, Food Anal. Methods, 12(2), 331-337 (2019). 10.1007/s12161-018-1364-1

175. "A Simple, Rapid Method for Gizzerosine Analysis in Fish Meal by Paper Electrophoresis"
Z.-H. Tao, M. Sato, K.-G. Wu, H. Kiyota, T. Yamaguchi, T. Nakano, Fish. Sci., 78, 923-926 (2012).

96. "Synthesis of (S)-Gizzerosine, a Potent Inducer of Gizzard Erosion in Chicks"
Y. Shimasaki, H. Kiyota, M. Sato, S. Kuwahara, Tetrahedron, 62, 9628-9634 (2006).

78. "Facile Synthesis of (S)-Gizzerosine, a Potent Inducer of Gizzard Erosion in Chicks, Using Successive Zinc-mediated and Palladium-catalyzed Coupling Reactions"
Y. Shimasaki, H. Kiyota, M. Sato, S. Kuwaharab Synthesis, 2005, 3191-3192.

The synthetic sample was offered to

Dr Zui-Hua Tao (Guangdong University Of Technology, China)

Dr Gareth Mann (Food & Drug Assurance Lab. (Pty) Ltd T/A FDA Lab., Pretoria, South Africa)

Prof. I. A. Samdal (National Veterinary Institute, Department of Chemistry, NORWAY)