62595-11-3

Basic information

• Product Name: L-TRYPTOPHAN (INDOLE-D5)
• Synonyms: L-TRYPTOPHAN-2',4',5',6',7'-D5 (INDOLE-D5);L-TRYPTOPHANE-2',4',5',6',7'-D5;L-TRYPTOPHAN (INDOLE-D5);L-Tryptophan-d5;(-)-1H-Indole-3-alanine-d5;(+/-)-Tryptophan-d5;L-α-AMino-3-indolepropionic Acid-d5;l-α-AMinoindole-3-propionic Acid-d5
• CAS NO: 62595-11-3
• Molecular Formula: C₁₁H₁₂N₂O₂
• Molecular Weight: 209.26
• Product Categories: Alphabetical Listings;Amino Acids;Amino AcidsStable Isotopes;Stable Isotopes;Amino Acids & Derivatives;Isotope Labelled Compounds
• Mol File: 62595-11-3.mol
• Article Data: 4

Chemical Properties

• Melting Point: 280-285 °C (dec.)(lit.)
• Boiling Point: 447.9 °C at 760 mmHg
• Flash Point: 224.7 °C
• Appearance: /
• Density: 1.396 g/cm³
• Storage Temp.: Refrigerator
• Solubility: Aqueous Acid (Slightly), Aqueous Base (Slightly), Methanol (Slightly, Sonicated,
• CAS DataBase Reference: L-TRYPTOPHAN (INDOLE-D5)(CAS DataBase Reference)
• NIST Chemistry Reference: L-TRYPTOPHAN (INDOLE-D5)(62595-11-3)
• EPA Substance Registry System: L-TRYPTOPHAN (INDOLE-D5)(62595-11-3)

Safety Data

• WGK Germany: 2
• Hazardous Substances Data: 62595-11-3(Hazardous Substances Data)

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 articles and documents

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.

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.