Leucine, 3-mercapto- (6CI,9CI)

Base Information

• Chemical Name: Leucine, 3-mercapto- (6CI,9CI)
• CAS No.: 98278-26-3
• Molecular Formula: C6H13 N O2 S
• Molecular Weight: 163.241
• Mol file: 98278-26-3.mol

Synonyms:Leucine, 3-mercapto- (6CI,9CI)

Chemical Property of Leucine, 3-mercapto- (6CI,9CI)

Chemical Property:

• PSA: 102.12000
• LogP: 1.05300

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• General Description: Leucine, 3-mercapto- (6CI,9CI), also known as β-mercaptoleucine, is a modified amino acid used in native chemical ligation (NCL) for protein synthesis. It enables efficient ligation at Xaa-Leu sites, followed by desulfurization to yield native peptides. This approach broadens the applicability of NCL, particularly for proteins with challenging sequences, such as those containing multiple cysteine residues, as demonstrated in the synthesis of HIV-1 Tat protein. Leucine, 3-mercapto- (6CI,9CI) expands the toolkit for chemical protein synthesis, facilitating the production of post-translationally modified analogues for research.

Technology Process of Leucine, 3-mercapto- (6CI,9CI)

There total 1 articles about Leucine, 3-mercapto- (6CI,9CI) which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.9%

(2RS,4RS)-2-isopropyl-5,5-dimethylthiazolidine-4-carbocyclic acid → 2-amino-3-mercapto-4-methylpentanoic acid (98278-26-3) + isobutyraldehyde (78-84-2)

Guidance literature:

With water; at 90 ℃; Column which a strongly acidic cation exchanger in the H+ form;

Refernces

Protein synthesis assisted by native chemical ligation at leucine

10.1002/cbic.201000168

The study explores an innovative strategy for synthesizing proteins using native chemical ligation (NCL) at Xaa-Leu sites, facilitated by β-mercaptoleucine and followed by desulfurization. The researchers synthesized β-mercaptoleucine through a series of chemical reactions starting from threo-β-hydroxy-l-leucine, involving conversion to a methyl ester derivative, formation of a p-nitrosulfonamide, ring closure to an aziridine, and BF3·OEt2-mediated ring opening with PMB-SH. This β-mercaptoleucine was then used in model peptides to test ligation with thioester peptides bearing different amino acids at the C-terminus (Gly, Ala, Ser, and Leu). The ligation products were successfully desulfurized to achieve the desired peptides. The strategy was further applied to the total chemical synthesis of HIV-1 Tat protein, overcoming challenges posed by the presence of multiple cysteine residues. The study demonstrates the potential of this new ligation chemistry to expand the scope of protein synthesis, enabling the creation of various post-translationally modified protein analogues for functional and structural analysis.

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