51514-17-1

Basic information

• Product Name: L-Alanine, N-glycyl-, methyl ester
• CAS NO: 51514-17-1
• Molecular Formula: C6H12N2O3
• Molecular Weight: 160.173
• Mol File: 51514-17-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: L-Alanine, N-glycyl-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: L-Alanine, N-glycyl-, methyl ester(51514-17-1)
• EPA Substance Registry System: L-Alanine, N-glycyl-, methyl ester(51514-17-1)

Safety Data

• Hazardous Substances Data: 51514-17-1(Hazardous Substances Data)

Upstream product

• 95083-50-4 methyl 2-(2-((t-butoxycarbonyl)amino)-ethanamido)propanoate 

Downstream Products

• 87532-24-9 N-carbobenzoxy-L-S-(acetamidomethyl)cysteinylglycyl-L-alanine methyl ester 
• 87532-23-8 Z-Cys-Gly-Ala-OMe 
• 13264-88-5 (S)-(-)-2-methylpiperazine dihydrochloride 
• 4526-77-6 (S)-3-methyl-2,5-piperazinedione 
• 88547-15-3 3-methyl-piperazine-2,5-dione 
• 87363-82-4 Boc-(L)-Leu-ΔPhe-Gly-(L)-Ala-OMe 

Relevant articles and documents

Synthesis of Histidine-Containing Oligopeptides via Histidine-Promoted Peptide Ligation

Histidine-containing peptides are valuable therapeutic agents for a treatment of neurodegenerative diseases. However, the synthesis of histidine-containing peptides is not trivial due to the potential of imidazole sidechain of histidine to act as a nucleophile if unprotected. A peptide ligation method utilizing the imidazole sidechain of histidine has been developed. The key imidazolate intermediate that acts as an internal acyl transfer catalyst during ligation is generated by deprotonation. Transesterification with amino acids or peptides tethered with C-terminal thioester followed by N→N acyl shifts led to the final ligated products. A range of histidine-containing dipeptides could be synthesized in moderate to good yields via this method without protecting the imidazole sidechain. The protocol was further extended to tripeptide synthesis via a long-range N→N acyl transfer, and tetrapeptide synthesis.

"Backdoor Induction" of chirality in asymmetric hydrogenation with rhodium(I) complexes of amino acid substituted triphenylphosphane ligands

This paper describes the synthesis and characterization of 5-(diphenylphosphanyl)isophthalic acid bioconjugates (Lig-[R]2). In addition to symmetrically disubstituted conjugates with amino acids, peptides or amines, a convenient one-pot, two-step procedure for the synthesis of conjugates bearing two different substituents is reported. The 28 prepared phosphanes were used as monodentate ligands in the rhodium(I)-catalyzed hydrogenation of 2-acetamidoacrylate and (Z)-α-acetamidocinnamate. The ligand with the smallest side-chain substituents Lig-[Ala-OMe]2 (1a) revealed the highest selectivity, with up to 84 % ee. The catalysts presented herein are models of artificial metalloenzymes in which the outer-coordination sphere controls the selectivity in catalysis. The chirality of distant hydrogen-bonded amino acids is transmitted by "backdoor induction" to the prochiral RhI center. Models of artificial metalloenzymes are presented in which the outer-coordination sphere controls the selectivity in catalysis. The chirality of distant hydrogen-bonded amino acids or amines is transmitted by "backdoor induction" to the prochiral RhI center. Copyright