66959-86-2

Basic information

• Product Name: Boc-N-Me-Met-OH
• Synonyms: Boc-N-Me-Met-OH
• CAS NO: 66959-86-2
• Molecular Formula: C₁₁H₂₁NO₄S
• Molecular Weight: 263.35374
• Product Categories: amino acids
• Mol File: 66959-86-2.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Boc-N-Me-Met-OH(CAS DataBase Reference)
• NIST Chemistry Reference: Boc-N-Me-Met-OH(66959-86-2)
• EPA Substance Registry System: Boc-N-Me-Met-OH(66959-86-2)

Safety Data

• Hazardous Substances Data: 66959-86-2(Hazardous Substances Data)

Upstream product

• 2488-17-7 Boc-Met(O)-OH 
• 2488-15-5 N-tert-butoxycarbonyl-L-methionine 
• 1393121-77-1 Boc-N-MeMet(O)-OH 
• 225386-53-8 (4S)-N-tert-butyloxycarbonyl-4-(2-methylthioethyl)-1,3-oxazolidin-5-one 
• 74-88-4 methyl iodide 

Downstream Products

• 1393122-34-3 Boc-N-MeMet-Sar-Sar-D-Phe-NH₂ 
• 66959-89-5 {(S)-1-[((S)-1-Carbamoyl-3-methylsulfanyl-propyl)-methyl-carbamoyl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester 

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.

Heterocyclic inhibitors of farnesyl protein transferase

Inhibition of farnesyl protein transferase is effected by compounds of the formula its enantiomers, diastereomers, pharmaceutically acceptable salts, prodrugs or solvates thereof, wherein:, A1 and A2 are each independently H, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, phenyl or substituted phenyl;, G1 is S or O;, G2 is H, -C(O)OH, -C(O)NH2, 5-tetrazolyl, -C(O)N(R7)OH or -CH2OH;, X is O or R8N;, Y and Z are each independently -CH2- or -C(O)-;, R1, R2, R3, R4, R5, R6 and R7 are each independently H or alkyl;, R1 may also be alkanoyl, R1 and A1 taken together may be -(CH2)m;, R8 is H, alkyl, phenyl, phenylalkyl, substituted phenyl, (substituted phenyl)alkyl or -C(O)R9;, R9 is H, alkyl, phenyl, phenylalkyl, substituted phenyl or (substituted phenyl)alkyl;, m is 3 or 4;, n is 0, 1 or 2;, p is 0, 1 or 2; and, q is 0 or 1, with the proviso that when p is 0, then q is also 0.