16946-96-6

Basic information

• Product Name: 2,5-Pyrrolidinedione, 1-[[N-[N-[(phenylmethoxy)carbonyl]-L-alanyl]-L-alanyl]oxy]-
• CAS NO: 16946-96-6
• Molecular Formula: C18H21N3O7
• Molecular Weight: 391.381
• Mol File: 16946-96-6.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2,5-Pyrrolidinedione, 1-[[N-[N-[(phenylmethoxy)carbonyl]-L-alanyl]-L-alanyl]oxy]-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Pyrrolidinedione, 1-[[N-[N-[(phenylmethoxy)carbonyl]-L-alanyl]-L-alanyl]oxy]-(16946-96-6)
• EPA Substance Registry System: 2,5-Pyrrolidinedione, 1-[[N-[N-[(phenylmethoxy)carbonyl]-L-alanyl]-L-alanyl]oxy]-(16946-96-6)

Safety Data

• Hazardous Substances Data: 16946-96-6(Hazardous Substances Data)

Upstream product

• 16012-70-7 benzyloxycarbonyl-L-alanyl-L-alanine 
• 90704-86-2 bis(N-hydroxysuccinimide) sulfite 
• 74124-79-1 di(succinimido) carbonate 
• 6066-82-6 1-hydroxy-pyrrolidine-2,5-dione 

Downstream Products

• 98839-17-9 N-(benzyloxycarbonyl)-L-alanyl-L-alanyl-DL-2-aminopimelic acid 
• 110512-41-9 methyl N--8-amino-2,6-anhydro-3,8-dideoxy-D-glycero-D-talo-octonate 
• 177657-11-3 Z-Ala-Ala-Leual 

Relevant articles and documents

Synthesis and stereoselective C-C bond-forming reactions of peptide aldehydes

The reaction of the activated form of N-protected amino acids 6 and 10 or peptides 14 and 18 with chiral amino alcohols derived from the corresponding α-amino acids affords peptide alcohols which can be oxidized under Swern conditions to produce the corresponding peptide aldehydes 9, 12, 16 and 20. The rational synthesis of diastereomeric di- and tripeptide aldehydes, e.g., (S,S)- or (R,S)-dipeptides as well as (S,S,S)- or (R,S,S)-tripeptides is possible by proper choice of the respective building blocks [(S)- versus (R)-amino acids]. The compounds can be prepared without any undesired α-epimerization. However, the long-term configurational stability depends upon the configuration at the remote stereogenic center, e.g., (R,S)-dipeptide aldehydes epimerize faster than the (S,S) diastereomers. Di- and tripeptide aldehydes 9, 12, 16 and 20 undergo chelation-controlled Grignardtype additions with Me2CuLi that involve little or no undesired α-epimerization. The (S,S)- and (R,S)-dipeptide aldehydes 9 and 12 undergo chelation-controlled pinacol reactions induced by the low-valent vanadium reagent [V2Cl3(THF)6]2[Zn2Cl 6]. The major products in both cases are the corresponding C2-symmetric diols 33 and 36, respectively, which are of interest as potential HIV-protease inhibitors. The degree of stereoselectivity is significantly higher in the case of the (S,S)-dipeptide aldehydes relative to the (R,S) analogs, an observation which can be explained on the basis of three-point binding of the peptides to vanadium. VCH Verlagsgesellschaft mbH, 1996.

Peptides of 2-aminopimelic acid: Antibacterial agents that inhibit diaminopimelic acid biosynthesis

Succinyl-CoA:tetrahydrodipicolinate-N-succinyltransferase is a key enzyme in the biosynthesis of diaminopimelic acid (DAP), a component of the cell wall peptidoglycan of nearly all bacteria. This enzyme converts the cyclic precursor tetrahydrodipicolinic

Chromophoric substrates. VI. The specificity of collagenase

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