Boc-3-Iodo-L-alanine methyl ester
[CAS# 93267-04-0]

Identification

• Classification: Biochemical >> Amino acids and their derivatives >> Alanine derivatives
• Name: Boc-3-Iodo-L-alanine methyl ester
• Synonyms: BOC-ß-IODO-ALA-OME
• Molecular Formula: C₉H₁₆INO₄
• Molecular Weight: 329.13
• Protein Sequence: X
• CAS Registry Number: 93267-04-0
• EC Number: 640-460-5
• SMILES: CC(C)(C)OC(=O)N[C@@H](CI)C(=O)OC

Properties

• Density: 1.6±0.1 g/cm³ Calc.^*
• Melting point: 50 - 52 °C (Expl.)
• Boiling point: 356.5±32.0 °C 760 mmHg (Calc.)^*
• Flash point: 169.4±25.1 °C (Calc.)^*
• Index of refraction: 1.513 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319
Eye irritation	Eye Irrit.	2	H319

Discovery and Applications

Boc-3-Iodo-L-alanine methyl ester is a chemical compound that belongs to the family of protected amino acids, specifically a derivative of L-alanine. The molecule consists of a Boc (tert-butyloxycarbonyl) protective group attached to the amino group, an iodo group at the 3-position of the alanine side chain, and a methyl ester group at the carboxyl position.

The Boc group is commonly used in peptide synthesis and organic chemistry to protect the amino group of amino acids during the formation of peptide bonds. The iodo group at the 3-position is a valuable functional group in organic synthesis, often utilized in electrophilic substitution reactions, and contributes to the compound's reactivity in various transformations.

The main application of Boc-3-Iodo-L-alanine methyl ester is in the field of peptide synthesis. The protective Boc group allows for the selective and controlled introduction of amino acids into growing peptide chains. The iodo group enables further functionalization or coupling with other reagents, facilitating the design and synthesis of more complex peptide sequences. The methyl ester group on the carboxyl group enhances the compound's solubility and reactivity, which is useful for various chemical reactions and purification processes.

Additionally, the compound's use extends to the synthesis of biologically active molecules, particularly in the context of drug discovery and medicinal chemistry. The functionalization of the alanine structure with an iodo group provides a versatile building block for the preparation of novel compounds that can potentially exhibit pharmacological activity.

Boc-3-Iodo-L-alanine methyl ester is a valuable intermediate in the preparation of peptides and other compounds in the chemical and pharmaceutical industries. It offers a functionalized structure that is useful in both synthetic chemistry and drug development, where its reactivity and ability to be incorporated into peptides or other bioactive molecules make it a useful tool for researchers.

References

2019. Decorating phenylalanine side-chains with triple labeled 13C/19F/2H isotope patterns. Journal of Biomolecular NMR,
DOI: 10.1007/s10858-024-00440-z

2024. Total Synthesis of Endolides A and B. Synlett: Accounts and Rapid Communications in Synthetic Organic Chemistry,
URL: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8218887

2011. New Routes to Lipophilic Amino Acids: Synthesis of Alkynyl and Fluoro-Containing Alanine Derivatives. Synlett,
DOI: 10.1055/s-0031-1290123