62595-11-3

Usage

Chemical Properties

White Solid

Synthetic route

L-Tryptophan (73-22-3) → <2,4,5,6,7-2H5>-L-tryptophan (62595-11-3)

Conditions	Yield
With diclazuril; mercaptoacetic acid In water-d2 at 110℃; for 4h;	99%
With trifluoroacetic acid-d1; water-d2 for 168h; Ambient temperature; repeated four times;	4.2 g
With DOTf at 20℃; for 8h;

<2,4,5,6,7-2H5>-L-tryptophan (62595-11-3) → C10H5(2)H5N2O (1159587-77-5)

Conditions	Yield
	25%

<2,4,5,6,7-2H5>-L-tryptophan (62595-11-3) → (Deuteroindolyl-3)-brenztraubensaeure (85163-57-1)

Conditions	Yield
With catalase at 25℃; for 2h; pH=7;	20%

<2,4,5,6,7-2H5>-L-tryptophan (62595-11-3) + Cypridina hilgendorfii → [D5]-cypridina luciferin

Conditions	Yield
biosynthesis;

p-acetoxycinnamoyl chloride (53901-95-4, 108608-06-6, 58523-18-5) + <2,4,5,6,7-2H5>-L-tryptophan (62595-11-3) → C22H15(2)H5N2O5

Conditions	Yield
In tetrahydrofuran at 20℃; for 72h;

4-acetoxy-3-methoxycinnamoyl chloride (50906-12-2) + <2,4,5,6,7-2H5>-L-tryptophan (62595-11-3) → C23H17(2)H5N2O6

Conditions	Yield
In tetrahydrofuran at 20℃; for 72h;

(E)-3,4-di-O-acetylcaffeoyl chloride (82592-68-5, 98631-72-2) + <2,4,5,6,7-2H5>-L-tryptophan (62595-11-3) → C24H17(2)H5N2O7

Conditions	Yield
In tetrahydrofuran at 20℃; for 72h;

<2,4,5,6,7-2H5>-L-tryptophan (62595-11-3) → L-[2,4,6,5,6,7-(2)H5]-tryptophan radical cation

Conditions	Yield
With cerium (IV) sulfate; sulfuric acid at 20℃;

Ribulose-5-phosphate (551-85-9) + <2,4,5,6,7-2H5>-L-tryptophan (62595-11-3) → C12H5(2)H5N2O2

Conditions	Yield
With isonitrile synthase at 20℃; for 0.333333h; Enzymatic reaction;

Upstream product

• 73-22-3 L-Tryptophan 

Relevant academic research and scientific papers

Biosynthesis of luciferin in the sea firefly, Cypridina hilgendorfii: L-tryptophan is a component in Cypridina luciferin

Feeding experiment to the marine ostracod crustacean, Cypridina (Vargula) hilgendorfii, using L-tryptophan labeled with deuterium at indole ring revealed that the labeled L-tryptophan was incorporated into Cypridina luciferin as a component and the animals were able to synthesize the luciferin in a de novo synthetic pathway.

The biosynthesis of the mould metabolites roquefortine and aszonalenin from L-[2,4,5,6,7-2H5]tryptophan

L-[2,4,5,6,7-2H5]Tryptophan was incorporated into roquefortine 2 by Penicillium roqueforti and aszonalenin 3 by Aspergillus zonatus with retention in each case of five deuterium atoms; the 5a-hydrogen of both metabolites is derived from the 2-hydrogen of tryptophan.

Hydrogen/deuterium exchange of cross-linkable α-amino acid derivatives in deuterated triflic acid

In this paper we report here a hydrogen/deuterium exchange (H/D exchange) of cross-linkable α-amino acid derivatives with deuterated trifluoromethanesulfonic acid (TfOD). H/D exchange with TfOD was easily applied to o-catechol containing phenylalanine (DOPA) within an hour. A partial H/D exchange was observed for trifluoromethyldiazirinyl (TFMD) phenylalanine derivatives. N-Acetyl-protected natural aromatic α-amino acids (Tyr and Trp) were more effective in H/D exchange than unprotected ones. The N-acetylated TFMD phenylalanine derivative afforded slightly higher H/D exchange than unprotected derivatives. An effective post-deuteration method for cross-linkable α-amino acid derivatives will be useful for the analysis of biological functions of bioactive peptides and proteins by mass spectrometry.

METHOD FOR DEUTERATION OR TRITIATION OF HETEROCYCLIC RING

The present invention relates to a method for deuteration of a heterocyclic ring, which comprises subjecting a compound having a heterocyclic ring to sealed refluxing state in a deuterated solvent in the presence of an activated catalyst selected form a palladium catalyst, a platinum catalyst, a rhodium catalyst, a ruthenium catalyst, a nickel catalyst and a cobalt catalyst. In accordance with a method of the present invention, a hydrogen atom belonging to a heterocyclic ring of a compound having a heterocyclic ring can be very efficiently deuterated because temperature of deuteration reaction can be maintained at higher than boiling point of the solvent. Further, a method for deuteration of the present invention can be applied widely to deuteration of various compounds having a heterocyclic ring which are liable to decomposition under supercritical conditions or acidic conditions, leading to industrial and efficient deuteration of a compound having a heterocyclic ring.