94343-39-2

Upstream product

• 17224-88-3 benzyl ((S)-1-(((S)-1-hydroxy-3-phenylpropan-2-yl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate 
• 3182-95-4 L-Phenylalaninol 
• 138772-65-3 tert-butyl ((2S)-1-(((2S)-1-hydroxy-3-phenylpropan-2-yl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate 
• 1161-13-3 N-Cbz-L-Phe 
• 2578-84-9 N-benzyloxycarbonyl-L-phenylalanine p-nitrophenyl ester 

Downstream Products

• 2566-22-5 DL-N-benzoylphenylalanine 
• 80780-41-2 aurantiamide acetate 
• 934221-37-1 N-(N-(4-dimethylaminomethylbenzoyl)-L-phenylalanyl)-L-phenylalanol 
• 58115-31-4 N-(N-benzoyl-L-phenylalanyl)-L-phenylalaninol 

Relevant academic research and scientific papers

Components of the Chinese drug 'Ti-ku-'pi'. Isolation and establishment of structure of a new dipeptide, lyciumamide

A new dipeptide, lyciumamide (1), was isolated from the Chinese crude drug 'Ti-ku-'pi', root bark of Lycium chinense MILL. (Solanaceae), and was shown by spectroscopy, chemical degradation, and synthesis to be N-benzoyl-L-phenylalanyl-L-phenylalaninol O-acetate (1).

Highly Enantioselective Construction of Fluoroalkylated Quaternary Stereocenters via Organocatalytic Dehydrated Mannich Reaction of Unprotected Hemiaminals with Ketones

A general organocatalytic asymmetric dehydrated Mannich reaction of fluoroalkyl hemiaminals with ketones is reported. In this Mannich reaction, previously less explored aryl ketones showed great reactivity. By virtue of this efficient method, a wide range of biologically active β-amino ketones were directly obtained. More importantly, two different intermediates involved in the reaction were detected and identified by 19F NMR and HRMS analysis. Furthermore, the synthetic utility of the products was demonstrated by the synthesis of the biologically active fluoroalkyl β-amino alcohols.

PHENYLALANINE DIPEPTIDE DERIVATIVES, COMPOSITIONS AND USE THEREOF

Disclosed are a compound of formula I, stereoisomers, pharmaceutically acceptable salts or hydrates thereof, a pharmaceutical composition comprising the smae, a process for preparing the same and use thereof. The compound may also be used to prepare a medicament to treat viral infections, especially to prepare a medicament to treat hepatitis B virus and human immunodeficiency virus with little toxic side effects.

Structure-activity study of endomorphin-2 analogs with C-terminal modifications by NMR spectroscopy and molecular modeling

Endomorphin-2 (EM-2) is a putative endogenous μ-opioid receptor ligand. To get insight into the important role of C-terminal amide group of EM-2, we investigated herein a series of EM-2 analogs by substitution of the C-terminal amide group with -NHNH2, -NHCH3, -N(CH3)2, -OCH3, -OCH2CH3, -OC(CH3)3, and -CH2-OH. Their binding affinity and bioactivity were determined and compared. Despite similar (analogs 1, 4, and 7) or decreased (analogs 2, 3,5, and 6) μ affinity in binding assays, all analogs showed low guinea pig ileum (GPI) and mouse vas deferens (MVD) potencies compared to their parent peptide. Interestingly, as for analogs 2 and 3 (a single and double N-methylation of C-terminal amide), the potency order with the Ki (μ) values was 2 > 3; for the C-terminal esterified analogs 4-6, the potency order with the Ki (μ) values was 4 > 5 > 6. Thus, we concluded that the steric hindrance of C-terminus might play an important role in opioid receptor affinity. We further investigated the conformational properties of these analogs by 1D and 2D 1H NMR spectroscopy and molecular modeling. Evaluating the ratios of cis- and trans-isomers, aromatic interactions, dihedral angles, and stereoscopic views of the most convergent conformers, we found that modifications at the C-terminal amide group of EM-2 affected these analog conformations markedly, therefore changed the opioid receptor affinity and in vitro bioactivity.