TRIFLUOROMETHANESULFONIC ACID-D

Name: TRIFLUOROMETHANESULFONIC ACID-D
SKU: ACM66178414-1
Rating: 5 (1 reviews)

CAS

66178-41-4

Catalog Number

ACM66178414-1

Category

Main Products

Molecular Weight

151.08

Molecular Formula

CDF3O3S

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Specification

Synonyms

Methanesulfonic acid-D, 1,1,1-trifluoro-

Appearance

Colorless liquid

Hydrogen/Deuterium Exchange of Cross-Linkable α-Amino Acid Derivatives in Deuterated Trifluoromethanesulfonic Acid

H/D exchange of photophore containing aromatic α-amino acid in trifluoromethanesulfonic acid-D.

Wang, Lei, et al. Bioscience, Biotechnology, and Biochemistry, 2014, 78(7), 1129-1134.

This study presented a technique for the effective hydrogen/deuterium (H/D) exchange of natural aromatic α-amino acids and their peptides using trifluoromethanesulfonic acid-D (TfOD) at temperatures below room temperature, while maintaining the stereochemistry.
· General Procedures for H/D Exchange with TfOD
Cross-linkable aromatic α-amino acid derivatives (0.25 mM) were dissolved in 0.9 mL of TfOD (10 mM) at a controlled temperature. The reaction mixture was then diluted with 0.6 mL of H2O, after which 1H-NMR and ESI-TOF mass spectrometry were performed for analysis.
· General Procedures for Acetylation of Aromatic α-Amino Acid Derivatives
The acetylation process started with 0.4 mM aromatic α-amino acid derivatives dissolved in 2 mL of methanol before adding 0.8 mM acetic anhydride gradually at a maintained temperature of 40 °C. After stirring the mixture overnight at the set temperature, concentrated it and used silica column chromatography to purify the residue which resulted in pure N-acetyl compounds with a yield of 60-75%.
· Key Findings
H/D exchange using TfOD was efficiently conducted on o-catechol-containing phenylalanine (DOPA) within one hour. Some partial H/D exchange was noted for trifluoromethyldiazirinyl (TFMD) phenylalanine derivatives. The N-acetyl-protected natural aromatic α-amino acids (tyrosine and tryptophan) showed improved efficacy in H/D exchange compared to their unprotected counterparts. The N-acetylated TFMD phenylalanine derivative exhibited a slightly higher rate of H/D exchange than the unprotected derivatives.

Deuterated Trifluoromethanesulfonic Acid Facilitates Hydrogen-Deuterium Exchange of Histidine and Histamine

Hydrogen/deuterium exchange of L/D-histidine in TfOD.

Tachrim, Zetryana Puteri, et al. Heterocycles, 2020, 101(1), 357-362.

The acidic deuterated trifluoromethanesulfonic acid (TfOD) was proved effective for hydrogen-deuterium exchange (H-D exchange) reactions in aromatic structures. The research employed TfOD as a method to perform effective hydrogen-deuterium exchange on natural aromatic α-amino acids and their peptides while mainly analyzing histidine and histamine.
Key Findings
L- and D-histidine (L-1 and D-1) experienced H-D exchange when exposed to TfOD at 130 °C over several hours. The α-position reached around 80% D after 48 hours of exchange whereas the 5-position attained roughly 70% D at 120 hours while the 2-position maintained a stable 30% D throughout the exchange period. High levels of deuterium incorporation at the α-position indicate a possible reduction in histidine's optical purity through the reaction. The TfOH solution showed optical rotations of +17 for L-histidine and -17 for D-histidine that did not change after 12 hours at -20 °C. The optical rotation became zero after heating at 130 °C for 12 hours.
Histamine showed a deuterium incorporation pattern that mirrored histidine's pattern with 87% D at the 5-position and 40% D at the 2-position. Histidine's imidazole 2-position incorporated deuterium under acidic DCl conditions when heated to 180 °C. The findings indicate that increasing the temperature is essential to promote hydrogen-deuterium exchange at the 2-position within the imidazole rings of histidine and histamine during TfOD reactions.

What is the molecular formula of TRIFLUOROMETHANESULFONIC ACID-D?

The molecular formula of TRIFLUOROMETHANESULFONIC ACID-D is CHF3O3S.

When was TRIFLUOROMETHANESULFONIC ACID-D created and modified?

It was created on August 8, 2005, and last modified on October 21, 2023.

What is the molecular weight of TRIFLUOROMETHANESULFONIC ACID-D?

The molecular weight of TRIFLUOROMETHANESULFONIC ACID-D is 151.09 g/mol.

What is the IUPAC name of TRIFLUOROMETHANESULFONIC ACID-D?

The IUPAC name of TRIFLUOROMETHANESULFONIC ACID-D is deuterio trifluoromethanesulfonate.

What is the InChI of TRIFLUOROMETHANESULFONIC ACID-D?

The InChI of TRIFLUOROMETHANESULFONIC ACID-D is InChI=1S/CHF3O3S/c2-1(3,4)8(5,6)7/h(H,5,6,7)/i/hD.

What is the InChIKey of TRIFLUOROMETHANESULFONIC ACID-D?

The InChIKey of TRIFLUOROMETHANESULFONIC ACID-D is ITMCEJHCFYSIIV-DYCDLGHISA-N.