860013-16-7

Basic information

• Product Name: N-(N-carbobenzyloxy-L-alanyl)-(2S)-2-phenylglycine tert-butyl ester
• Synonyms: N-(N-carbobenzyloxy-L-alanyl)-(2S)-2-phenylglycine tert-butyl ester
• CAS NO: 860013-16-7
• Molecular Weight: 412.486
• Mol File: 860013-16-7.mol

Chemical Properties

• CAS DataBase Reference: N-(N-carbobenzyloxy-L-alanyl)-(2S)-2-phenylglycine tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-(N-carbobenzyloxy-L-alanyl)-(2S)-2-phenylglycine tert-butyl ester(860013-16-7)
• EPA Substance Registry System: N-(N-carbobenzyloxy-L-alanyl)-(2S)-2-phenylglycine tert-butyl ester(860013-16-7)

Safety Data

• Hazardous Substances Data: 860013-16-7(Hazardous Substances Data)

Upstream product

• 2935-35-5 (S)-2-phenylglycine 
• 1142-20-7 N-Cbz-Ala 

Downstream Products

• 263162-50-1 (2S)-({N-[(3,5-difluorophenyl)acetyl]-L-alanyl}amino)(phenyl)acetic acid 
• 208255-80-5 ((S)-tert-butyl 2-((S)-2-(2-(3,5-difluorophenyl)acetamido)propanamido)-2-phenylacetate) 
• 867022-09-1 6-[(S)-2-((S)-2-tert-Butoxycarbonylamino-propionylamino)-2-phenyl-acetylamino]-hexanoic acid (S)-2-((R)-3,4-bis-benzyloxy-5-oxo-2,5-dihydro-furan-2-yl)-2-hydroxy-ethyl ester 
• 867021-96-3 N-[N-(tert-butyloxycarbonyl)-L-alanyl]-(2S)-2-phenylglycine 
• 327052-53-9 N-(L-alanyl)-(2S)-2-phenylglycine tert-butyl ester 

Relevant articles and documents

Epimerization-Free C-Term Activation of Peptide Fragments by Ball Milling

Peptides were produced in high yields and, if any, very low epimerization, by mechanochemical coupling of peptide fragments containing highly epimerization-prone and/or highly hindered amino acids at C-term. Ball milling was clearly identified as the key element enabling one to obtain such results.

Enhanced delivery of γ-secretase inhibitor DAPT into the brain via an ascorbic acid mediated strategy

Inhibition of γ-secretase, one of the enzymes responsible for the cleavage of the amyloid precursor protein (APP) to produce pathogenic Aβ peptides, is an attractive approach for the treatment of Alzheimer's disease. We designed a γ-secretase inhibitor bearing an ascorbic acid moiety which allows a specific delivery of the drug to the brain. Through, on the one hand, Aβ peptide production measurements by specific in vitro assays (γ-secretase cell free assay and cell based assay on HEK 293 APP transfected cells) and on the other hand through pharmacokinetic studies on animal models, the new inhibitor shows a good pharmacokinetic profile as well as a potent γ-secretase inhibitory activity In vitro. From the obtained results, it is expected that drug 2 will be mainly delivered to the CNS with a low diffusion in the peripheral tissues. Consequently the side effects of this γ-secretase inhibitor on the immune cells could be reduced. The Royal Society of Chemistry 2005.

Design of β-secretase inhibitors by introduction of a mandelyl moiety in DAPT analogues

We report the synthesis of two series of compounds with 3,5-difluoromandelyl-alanyl or 3,5-difluorophenylacetylalany1 backbones coupled to various heterocyclic or peptidic moieties. These two series of compounds were evaluated for their inhibitory propert

Parallel synthesis of DAPT derivatives and their γ-secretase- inhibitory activity

Parallel synthesis of the C-terminal-modified DAPT (1) derivatives was accomplished utilizing our novel resin 7. Condensation reaction of the N-acylamino acid 10 with the amines 11a-o proceeded smoothly to give the corresponding amides 6a-o without any epimerization. Among the analogues, the benzophenonemethyl amide derivative 6o showed 30 times more potent activity than the original DAPT (1).