Tugas kelompok KBA-sub tema-Shikimic Pathway 15 April 2020

Johann Frederik Eijkman

Johan Fredrik Eykman or Johann Frederik Eijkman (19 January 1851 – 7 January 1915) was a Dutch
chemist. He is one of the eight children of Christiaan Eijkman, the headmaster of a local school, and Johanna
Alida Pool. His brother Christiaan Eijkman (1858-1930) was a physician and professor of physiology whose
demonstration that beriberi is caused by poor diet led to the discovery of vitamins. Together with Sir
Frederick Hopkins, his brother received the Nobel Prize for Physiology or Medicine.
He was hired during the Meiji period, a Japanese era which extended from September 1868 through July
1912. During his stay in Japan, he was the first to isolate shikimic acid in 1885 from the Japanese flower
shikimi (シキミ, the Japanese star anise, Illicium anisatum).

Shikimic acid
The Japanese star anise - Illicium anisatum, to give it its proper name, or shikimi as it’s known in Japan –
is an elegant plant. Broad green leaves surround white many-petalled flowers, which in turn give rise to
eight-pointed star-shaped seeds. It’s also the source of the chemical shikimic acid, first purified by Dutch
chemist Johan Fredrik Eykman in 1885. Composed solely of carbon, hydrogen and oxygen, shikimic acid
is an important starting ingredient in several multi-step biochemical manufacturing processes found in a
wide range of lifeforms from bacteria and fungi to parasites and plants.

This so-called ‘shikimate pathway’ transforms shikimic acid into molecules such as the amino
acids phenylalanine and tryptophan (two of the building blocks of proteins) and other useful
chemicals. Importantly, this pathway isn’t found in humans and other animals. Not only is this
relevant from an industrial point of view, as we’ll see later, but it also means that because we
can’t make them ourselves, we have to make sure we eat foods containing phenylalanine and
tryptophan, otherwise we’re in serious trouble. Shikimic Acid, A tri-hydroxy cyclohexene
carboxylic acid important in biosynthesis of so many compounds that the shikimate pathway is
named after it. Shikimic acid, more commonly known as its anionic form shikimate, is a
cyclohexene, a cyclitol and a cyclohexanecarboxylic acid. It is an important biochemical
metabolite in plants and microorganisms. Its name comes from the Japanese flower shikimi,
from which it was first isolated in 1885 by Johan Fredrik Eykman. The elucidation of its
structure was made nearly 50 years later. It appears in the list of Group 3 carcinogens of the
International Agency for Research on Cancer. Group 3 means that the agent is not classifiable as
to its carcinogenicity to humans. Nevertheless, it is recommended to roast tree fern fronds, a
speciality called fiddlehead. These fronds are edible, but must be roasted first to remove shikimic
acid. Shikimic acid is also the glycoside part of some hydrolysable tannins.

BAHAN DISKUSI
1. Buat kelompok diskusi terdiri 3 mahasiswa
2. Carilah senyawa bahan alam : scopoletin, epigallocatechin, vitamin K2. Gambarkan
strukturnya.
3. Dari soal n0.2 diatas. Diskusikan (bila perlu gambarkan) ,Buktikan bahwa senyawa tersebut
berasal dari jalur shikimate,
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Catatan : materi harus sdh dikumpulkan kembali sampai hari Selasa 14 April 2020.