3-Iodo-L-tyrosine

H-Tyr(3-I)-OH is an effective tyrosine hydroxylase inhibitor.

Solid

3-iodo-L-tyrosine is the monoiodotyrosine that is L-tyrosine carrying an iodo-substituent at position C-3 of the benzyl group. It has a role as a human metabolite, an EC 1.14.16.2 (tyrosine 3-monooxygenase) inhibitor and a mouse metabolite. It is a L-tyrosine derivative, a non-proteinogenic L-alpha-amino acid and a monoiodotyrosine. It is a tautomer of a 3-iodo-L-tyrosine zwitterion.|3-Iodotyrosine is an intermediate in the production of thyroid hormones and derivative of tyrosine where the carbon at position 3 in the benzyl group has been iodinated by thyroid peroxidase. 3-iodotyrosine (mono-iodotyrosine) can be further iodinated by thyroid peroxidase to form di- and tri-iodo forms. Mono-iodotyrosine can combine with a di-iodotyrosine to form triiodothyronine (T3) and two di-iodotyrosines can combine to form thyroxine (T4).

To a 3000 L flask, were added A6 (147.3 kg, 813 mol, 1 equiv.) and conc. NH3H2O (25percent, 1980 kg, 13.5 w). The white suspension was cooled to -10-0 °C. (223 kg, 878 mol, 1.08 equiv.) was added in 40 portions over a period of ~5 hrs. at -10-0 °C. The solution was stirred at -10-0 °C for ~2 hrs. (a sample was taken from the mixture and diluted with water for IPC on HPLC: 86.4 Apercent of A7 & 11.3 Apercent of bis-iodide (not shown in Scheme 2B) and 2.3 Apercent of A6 remained). It was then concentrated under vacuum at 0-40 °C for -28 hrs. until the pH of the residue dropped to 9.6. The residue solution was cooled to 20-30 °C. Aqueous HCl (18 wpercent) was added dropwise at 20-30 °C over 10 h to adjust the pH to 8 before A7 (0.25 kg) was added as seeds. After the mixture was continuously stirred for ~1 h at 20-30 °C, the pH of the mixture was continuously adjusted using aqueous HCl (18 wpercent) to 7.4 over -3 hrs. and 6.6 over ~1 hr., and stirred for 1 hr. at each pH stage. The resultant was stirred at 20-30 °C for 2 h (a total of -1200 kg of 18 wpercent aq. HCl was used for crystallization). The slurry was centrifuged. The wet cake was washed twice with water (230 kg, 1.6 w, each) and then twice with acetone (230 kg, 1.6 w, each). The solid was dried under vacuum at 50-60 °C for ~48 hrs. to afford 156.6 kg of A7 with 96 Apercent purity & 2.5 wpercent water content as a light brown solid in 62.6percent yield (uncorrected; subtract 0.25 kg of A7 seed).

A novel flavoprotein responsible for iodide salvage in thyroid glands. A tyrosine hydroxylase inhibitor.

Molecular Weight:307.08
XLogP3:-1.1
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:3
Exact Mass:306.97054
Monoisotopic Mass:306.97054
Topological Polar Surface Area:83.6
Heavy Atom Count:14
Complexity:212
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes