141806-16-8

Basic information

• Product Name: O-(2,6-dichlorobenzyl)-L-homotyrosine
• Synonyms: O-(2,6-dichlorobenzyl)-L-homotyrosine
• CAS NO: 141806-16-8
• Molecular Weight: 354.233
• Mol File: 141806-16-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: O-(2,6-dichlorobenzyl)-L-homotyrosine(CAS DataBase Reference)
• NIST Chemistry Reference: O-(2,6-dichlorobenzyl)-L-homotyrosine(141806-16-8)
• EPA Substance Registry System: O-(2,6-dichlorobenzyl)-L-homotyrosine(141806-16-8)

Safety Data

• Hazardous Substances Data: 141806-16-8(Hazardous Substances Data)

Upstream product

• 110936-12-4 N-(methylcarbamoyl)homotyrosine methyl ester 
• 141899-12-9 L-homotyrosine hydrobromide 
• 20443-98-5 2,6-Dichlorobenzyl bromide 

Downstream Products

• 141806-21-5 (2S,3S,4S)-3-hydroxy-4-methyl-ProOMe-Thr-Homotyr-4-OH-Pro-Thr-α-N-(octyloxybenzoyl)-δ-CBZ-Orn 
• 141806-23-7 (2S,3S,4S)-3-hydroxy-4-methyl-Pro-Thr-Homotyr-4-OH-Pro-Thr-α-N-(octyloxybenzoyl)-δ-CBZ-Orn 
• 141806-20-4 Thr-O-CBZ-Homotyr-4-OH-Pro-Thr-α-N-(octyloxybenzoyl)-δ-CBZ-Orn 
• 141806-19-1 Thr-Honotyr-4-OH-Pro-Thr-α-N-(octyloxybenzoyl)-δ-CBZ-Orn 
• 141806-24-8 (2S,3S,4S)-3-hydroxy-4-methyl-Pro-Thr-Homotyr-4-OH-Pro-Thr-α-N-(octyloxybenzoyl)-Orn 
• 141806-25-9 cyclo-(2S,3S,4S)-3-hydroxy-4-methyl-Pro-Thr-Homotyr-4-OH-Pro-Thr-α-N-(octyloxybenzoyl)-Orn 
• 141806-18-0 Thr-Homotyr-4-OH-Pro-Thr-α-N-(octyloxybenzpyl)-Orn 
• 141806-22-6 (2S,3S,4S)-3-hydroxy-4-methyl-ProOMe-Thr-O-CBZ-Homotyr-4-OH-Pro-Thr-α-N-(octyloxybenzoyl)-δ-CBZ-Orn 
• 141806-17-9 O-(2,6-dichlorobenzyl)-α-N-t-Boc-L-homotyrosine 

Relevant articles and documents

Preparation and Structure-Activity Relationships of Simplified Analogues of the Antifungal Agent Cilofungin: A Total Synthesis Approach

The echinocandins are a well-known class of lipopeptides characterized by their potent antifungal activity against Candida species.The mechanism of action of the echinocandins is generally thought to be the inhibition of β-1,3-glucan synthesis, an important structural component in the cell wall of Candida species.Extensive structure-activity studies on the fatty acid side chain of echinocandin B (1) led to the preparation of the clinical candide cilofungin (4).However, little is known about the cyclic peptide.We now report the preparation, by solid-phase synthesis, of a series of simplified analogs of cilofungin in which the unusual amino acids found in the echinocandins were replaced with more readily accesible natural amino acids.The solid-phase approach to the total synthesis of these analogs allowed us to conveniently explore structural modifications that could not be accomlished by chemical modification of the natural product.The simplest analog 5 showed no biological activity.Structural complexity was then returned to the sytem in a systematic fashion so as to reapproach the original cilofungin structure.Antifungal activity and the inhibition of β-1,3-glucan synthesis were monitored at each step of the process, thereby revealing the basic structure-activity relationships of the amino acids and the minimal structural requirements for biological activity in the echinocandin ring system.The results suggests that the 3-hydroxy-4-methylproline residue enhances activity but the L-homotyrosine residue is crucial for both antifungal activity and the inhibition of β-1,3-glucan synthesis.