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

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

Uses

Used in Organic Synthesis:
BOC-MET(O)-OH is used as a building block in organic synthesis for its ability to participate in a wide range of chemical reactions without compromising its structural integrity.
Used in Pharmaceutical Research:
In pharmaceutical research, BOC-MET(O)-OH serves as a precursor for the preparation of various pharmaceuticals and biochemical reagents, contributing to the development of new drugs and therapeutic agents.
Used in Peptide and Protein Synthesis:
BOC-MET(O)-OH is utilized as a key component in the synthesis of peptides and proteins, where its protecting group facilitates controlled reactions and the formation of complex molecular structures.
Used in the Preparation of Biochemical Reagents:
BOC-MET(O)-OH is also employed in the preparation of biochemical reagents, where its stability and reactivity are essential for creating reliable and effective research tools.

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

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

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.