90119-83-8

Basic information

• Product Name: D-Phenylalanine, N-benzoyl-, 2-(benzoylamino)-3-phenylpropyl ester, (S)-
• CAS NO: 90119-83-8
• Molecular Formula: C32H30N2O4
• Molecular Weight: 506.601
• Mol File: 90119-83-8.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: D-Phenylalanine, N-benzoyl-, 2-(benzoylamino)-3-phenylpropyl ester, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: D-Phenylalanine, N-benzoyl-, 2-(benzoylamino)-3-phenylpropyl ester, (S)-(90119-83-8)
• EPA Substance Registry System: D-Phenylalanine, N-benzoyl-, 2-(benzoylamino)-3-phenylpropyl ester, (S)-(90119-83-8)

Safety Data

• Hazardous Substances Data: 90119-83-8(Hazardous Substances Data)

Upstream product

• 65-85-0 benzoic acid 
• 63-91-2 L-phenylalanine 
• 5267-65-2 (S)-N-(1-hydroxy-3-phenylpropan-2-yl)benzamide 
• 67736-12-3 (S)-2-Amino-3-phenyl-propionic acid (S)-2-benzoylamino-3-phenyl-propyl ester 
• 98-88-4 benzoyl chloride 
• 2566-22-5 N-benzoyl-L-phenylalanine 
• 1042715-33-2 C₂₅H₂₆N₂O₃ 
• 3182-95-4 L-Phenylalaninol 
• 849123-63-3 (S)-(S)-2-benzamido-3-phenylpropyl 2-(tert-butoxycarbonylamino)-3-phenylpropanoate 
• 1042715-31-0 (R)-(S)-2-benzamido-3-phenylpropyl 2-(tert-butoxycarbonylamino)-3-phenylpropanoate 

Relevant articles and documents

Asperphenamate biosynthesis reveals a novel two-module NRPS system to synthesize amino acid esters in fungi

Amino acid esters are a group of structurally diverse natural products with distinct activities. Some are synthesized through an inter-molecular esterification step catalysed by nonribosomal peptide synthetase (NRPS). In bacteria, the formation of the intra-molecular ester bond is usually catalysed by a thioesterase domain of NRPS. However, the mechanism by which fungal NRPSs perform this process remains unclear. Herein, by targeted gene disruption in Penicillium brevicompactum and heterologous expression in Aspergillus nidulans, we show that two NRPSs, ApmA and ApmB, are sufficient for the synthesis of an amino acid ester, asperphenamate. Using the heterologous expression system, we identified that ApmA, with a reductase domain, rarely generates dipeptidyl alcohol. In contrast, ApmB was determined to not only catalyse inter-molecular ester bond formation but also accept the linear dipeptidyl precursor into the NRPS chain. The mechanism described here provides an approach for the synthesis of new small molecules with NRPS as the catalyst. Our study reveals for the first time a two-module NRPS system for the formation of amino acid esters in nature.

Total synthesis and anticancer activity studies of the stereoisomers of asperphenamate and patriscabratine

All stereoisomers of asperphenamate 1a and patriscabratine 2a were achieved with a high yield, and total synthesis of 2a is firstly described here. The absolute configuration of patriscabratine was determined as (S,S). The compounds 1a-d and 2a-d have been tested by MTT assay in T47D, MDA-MB231, HL60, Hela and SGC-7901 cell lines in vitro. Among them, the (R,S) stereoisomer shows the strongest anticancer effects, while the (S,R) shows the weakest one.