34805-21-5

Basic information

• Product Name: BOC-MET(O)-OH
• Synonyms: N-ALPHA-TERT-BUTYLOXYCARBONYL-L-METHIONINESULFOXIDE;N-ALPHA-T-BUTOXYCARBONYL-L-METHIONINE SULFOXIDE;N-ALPHA-T-BOC-L-METHIONINE-D,L-SULFOXIDE;BOC-L-METHIONINE (O);BOC-L-MET(O)-OH;BOC-L-MET(O);BOC-L-METHIONINE SULFOXIDE;BOC-MET(O)-OH
• CAS NO: 34805-21-5
• Molecular Formula: C₁₀H₁₉NO₅S
• Molecular Weight: 265.33
• Product Categories: Amino Acid Derivatives;Amino Acids;Methionine [Met, M];Boc-Amino Acids and Derivative;Boc-Amino acid series
• Mol File: 34805-21-5.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 509.3 °C at 760 mmHg
• Flash Point: 261.8 °C
• Appearance: /Solid
• Density: 1.26 g/cm³
• Vapor Pressure: 9.48E-12mmHg at 25°C
• Refractive Index: 1.521
• Storage Temp.: Store at RT.
• PKA: 3.70±0.10(Predicted)
• CAS DataBase Reference: BOC-MET(O)-OH(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-MET(O)-OH(34805-21-5)
• EPA Substance Registry System: BOC-MET(O)-OH(34805-21-5)

Safety Data

• WGK Germany: WGK 2 water endangering
• Hazardous Substances Data: 34805-21-5(Hazardous Substances Data)

Usage

General Description

BOC-MET(O)-OH, also known as N-tert-butoxycarbonyl-L-methionine (Oxide), is a chemical compound used in organic synthesis and pharmaceutical research. It is a derivative of the amino acid L-methionine, with a tert-butoxycarbonyl (BOC) protecting group attached to the amino group and an oxygen atom attached to the sulfur atom. BOC-MET(O)-OH is commonly used as a building block in peptide and protein synthesis, as well as a precursor for the preparation of various pharmaceuticals and biochemical reagents. BOC-MET(O)-OH is known for its stability and compatibility with a wide range of chemical reactions, making it a valuable tool in the field of organic and medicinal chemistry.

InChI:InChI=1/C10H19NO5S/c1-10(2,3)16-9(14)11-7(8(12)13)5-6-17(4)15/h7H,5-6H2,1-4H3,(H,11,14)(H,12,13)/t7-,17?/m0/s1

Upstream product

• 2488-15-5 N-tert-butoxycarbonyl-L-methionine 

Downstream Products

• 83443-88-3 Boc-Met(O)-Asp(OBzl)-Phe-NH₂ 
• 123347-87-5 C₁₁₂H₁₄₀Cl₂N₁₄O₂₂S₂ 
• 63-68-3 L-methionine 
• 18917-24-3 gastrin-5 
• 66959-86-2 N-α-t-Boc-(S)-α-methylmethionine 

Relevant articles and documents

Study of intramolecular aminolysis in peptides containing N-alkylamino acids at position 2

Many peptides and proteins, containing Nα-alkylamino acids (including proline) at the second position, are prone to intramolecular aminolysis (IA) with elimination of N-terminal dipeptide sequence as 2,5-diketopiperazines (DKP). We synthesized a series of short peptides, containing N-alkylamino acids at position 2, and studied their stability in the presence of acetic acid and amines. The presence of side chains in the second and the third amino acid residues and alkylation at Nα of the third amino acid residue slowed down IA. Nα-Alkyl residue in the first amino acid residue impeded IA only in peptides, containing three or more residues. Side chains of the first amino acids did not affect significantly the cleavage rates. Acetic acid promoted IA more strongly than aqueous ammonia, while tertiary amines were less effective. Peptides with methionine-S-oxide residues were more labile than the unoxidized analogs, suggesting intramolecular assistance of the S-oxide group in aminolysis. Surprisingly, intermediate compounds of the formula Boc-Met-MeXaa-Sar-NHR underwent rapid cleavage (endopeptolysis) upon attempted acidolytic deprotection.