Tetrahedron has developed new synthetic processes allowing the industrial production of the following known compounds:
- L-(+)-ergothioneine, a well-known natural and powerful antioxidant
- S-methyl-L-ergothioneine, a new natural antioxidant
Tetrahedron has also designed new and proprietary antioxidants, which are selenoorganic compounds:
- The basic structure is NutraSelen® (THD-177) which is a novel organic source of selenium, in particular through its ability to be bioconverted into L-selenomethionine, the natural source of selenium in human and animals.
A licensing agreement was signed to use NutraSelen® in Animal Nutrition.
Tetrahedron is a supplier of NutraSelen® (see below) as well as of L-(+)-ergothioneine, S-methyl-L-ergothioneine and L-2-thiohistidine, which can be ordered on line (see below) according to our General Conditions of Sale ("Conditions générales de vente "). For request of quotation on larger quantities, please contact us.
| Product | CAS RN Molecular formula Molecular weight (g/mol) |
Purity* | To order** |
|---|---|---|---|
| (*) by 1H-NMR | (**) DDU | ||
NutraSelen®![]() |
873660-49-2 C5H10O3Se 197.1 |
≥98% | on request |
L-Ergothioneine![]() |
497-30-3 C9H15N3O2S 229.3 |
≥98% | semi-bulk on request |
S-Methyl-L-ergothioneine![]() |
- C10H17N3O2S 243.3 |
≥98% | |
L-2-Thiohistidine![]() |
2002-22-4 C6H9N3O2S 187.2 |
≥97% | semi-bulk on request |
For academics, free 100-mg samples of L-2-thiohistidine and NutraSelen® are available upon request.
Tetrahedron is also a supplier of the following series of compounds, which can be ordered on line (see below) according to our General Conditions of Sale ("Conditions générales de vente"):
A/ 2-Thioimidazoles compounds
| Product | CAS RN Molecular formula Molecular weight (g/mol) |
Purity* | To order** |
|---|---|---|---|
| (*) by 1H-NMR | (**) DDU | ||
D-Ergothioneine![]() |
- C9H15N3O2S 229.3 |
≥98% | |
D-2-Thiohistidine![]() |
- C6H9N3O2S 187.2 |
≥97% | |
D,L-2-Thiohistidine![]() |
13552-61-9 C6H9N3O2S 187.2 |
≥97% | |
| α-N-Methyl- L-2-thiohistidine ![]() |
- C7H11N3O2S 201.2 |
≥98% | |
| α-N,N-Dimethyl- L-2-thiohistidine ![]() |
170227-63-1 C8H13N3O2S 215.2 |
≥98% |
B/ Protected derivatives of 2-thiohistidine
With regard to the interesting properties of L-2-thiohistidine, its following series of derivatives have been designed to introduce it into peptides or polymers and thus provide the opportunity of investigating the properties of new and patentable compounds.
Series of S- or N-protected derivatives of 2-thiohistidine:
In this series, the following monoprotected compounds correspond to the general formula
- where P1=H and P2=Boc
- or P1=tBu, Mob or DNP and P2=H
Product* |
CAS RN Molecular formula Molecular weight (g/mol) |
Purity** | To order*** |
|---|---|---|---|
| (*) designation based on the adoption of "H-2-Thiohis-OH" for 2-thiohistidine (**) by 1H-NMR (***) DDU |
|||
| Boc-2-Thiohis-OH (THD-268) |
- C11H17N3O4S 287.3 |
≥95% | |
| H-2-Thiohis(tBu)-OH (THD-269) ![]() |
- C10H17N3O2S 243.3 |
≥95% | |
| H-2-Thiohis(Mob)-OH (THD-270) ![]() |
- C14H17N3O3S 307.4 |
≥95% | |
| H-2-Thiohis(DNP)-OH (THD-271) ![]() |
- C12H11N5O6S 353.3 |
≥95% | |
| Set of the 4 monoprotected compounds | |||
Series of S- and N-protected derivatives of 2-thiohistidine:
In this series, the following diprotected compounds correspond to the general formula
- where P1=tBu, Mob or DNP and P2=Boc, Fmoc, Z or Trt
Product* |
CAS RN Molecular formula Molecular weight (g/mol) |
Purity** | To order*** |
|---|---|---|---|
| (*) designation based on the adoption of "H-2-Thiohis-OH" for 2-thiohistidine (**) by 1H-NMR (***) DDU |
|||
| Boc-2-Thiohis(tBu)-OH (THD-272) ![]() |
- C15H25N3O4S 343.4 |
≥95% | |
| Fmoc-2-Thiohis(tBu)-OH (THD-273) ![]() |
- C25H27N3O4S 465.6 |
≥95% | |
| Z-2-Thiohis(tBu)-OH (THD-274) ![]() |
- C18H23N3O4S 377.5 |
≥95% | |
| Trt-2-Thiohis(tBu)-OH (THD-275) ![]() |
- C29H31N3O2S 485.6 |
≥95% | |
| Boc-2-Thiohis(Mob)-OH (THD-276) ![]() |
- C19H25N3O5S 407.5 |
≥95% | |
| Fmoc-2-Thiohis(Mob)-OH (THD-277) ![]() |
- C29H27N3O5S 529.6 |
≥95% | |
| Z-2-Thiohis(Mob)-OH (THD-278) ![]() |
- C22H23N3O5S 441.5 |
≥95% | |
| Trt-2-Thiohis(Mob)-OH (THD-279) ![]() |
- C33H31N3O3S 549.7 |
≥95% | |
| Boc-2-Thiohis(DNP)-OH (THD-280) ![]() |
- C17H19N5O8S 453.4 |
≥95% | |
| Fmoc-2-Thiohis(DNP)-OH (THD-281) ![]() |
- C27H21N5O8S 575.6 |
≥95% | |
| Z-2-Thiohis(DNP)-OH (THD-282) ![]() |
- C20H17N5O8S 487.4 |
≥95% | |
| Trt-2-Thiohis(DNP)-OH (THD-283) ![]() |
- C31H25N5O6S 595.6 |
≥95% | |
| Set of the 12 S- and N-protected compounds | |||
Series of S- and O-protected derivatives of 2-thiohistidine:
In this series, the following diprotected compounds correspond to the general formula
- where P1=tBu, Mob or DNP and P3=Me, Bn or All
Product* |
CAS RN Molecular formula Molecular weight (g/mol) |
Purity** | To order*** |
|---|---|---|---|
| (*) designation based on the adoption of "H-2-Thiohis-OH" for 2-thiohistidine (**) by 1H-NMR (***) DDU |
|||
| H-2-Thiohis(tBu)-OMe.2HCl (THD-284) ![]() |
- C11H19N3O2S,2HCl 330.3 |
≥95% | |
| H-2-Thiohis(tBu)-OBn.2HCl (THD-285) ![]() |
- C11H23N3O2S,2HCl 406.4 |
≥95% | |
| H-2-Thiohis(tBu)-OAll.2HCl (THD-286) ![]() |
- C13H21N3O2S,2HCl 356.3 |
≥95% | |
| H-2-Thiohis(Mob)-OMe.2HCl (THD-287) ![]() |
- C15H19N3O3S,2HCl 394.3 |
≥95% | |
| H-2-Thiohis(Mob)-OBn.2HCl (THD-288) ![]() |
- C21H23N3O3S,2HCl 470.4 |
≥95% | |
| H-2-Thiohis(Mob)-OAll.2HCl.H2O (THD-289) ![]() |
- C17H21N3O3S,2HCl,H2O 438.4 |
≥95% | |
| H-2-Thiohis(DNP)-OMe.2HCl.H2O (THD-290) ![]() |
- C13H13N5O6S,2HCl,H2O 458.3 |
≥95% | |
| H-2-Thiohis(DNP)-OBn.2HCl (THD-291) ![]() |
- C19H17N5O6S,2HCl 516.4 |
≥95% | |
| H-2-Thiohis(DNP)-OAll.2HCl (THD-292) ![]() |
- C15H17N5O7S,2HCl 466.3 |
≥95% | |
| Set of the 9 S- and O-protected compounds | |||
| Set of the 25 protected compounds | |||
































