141899-12-9

Basic information

• Product Name: L-Homotyrosine hydrobromide
• Synonyms: H-L-HTyr-OH*HBr;(S)-alpha-Amino-4-hydroxybenzenebutanoic acid hydrobromide;(S)-2-amino-4-(4-hydroxyphenyl)butanoic acid hydrobromide;L-HoMoTyr-OH L-HoMotyrosine.HBr;(αS)-AMino-4-hydroxy;H-L-HOTyr-OH·HBr;(S)-4-Hydroxy-homophenylalanine HBr;L-HomoTyr-OH·HBr
• CAS NO: 141899-12-9
• Molecular Formula: BrH*C₁₀H₁₃NO₃
• Molecular Weight: 276.13
• Product Categories: Tyrosine [Tyr, Y];Unusual Amino Acids;Amino Acids 13C, 2H, 15N;Amino hydrochloride;Amino Acids & Derivatives;Aromatics;Chiral Reagents
• Mol File: 141899-12-9.mol
• Article Data: 1

Chemical Properties

• Melting Point: 220-225°C
• Appearance: /
• Storage Temp.: Store at 0-5°C
• Solubility: DMSO, Methanol
• CAS DataBase Reference: L-Homotyrosine hydrobromide(CAS DataBase Reference)
• NIST Chemistry Reference: L-Homotyrosine hydrobromide(141899-12-9)
• EPA Substance Registry System: L-Homotyrosine hydrobromide(141899-12-9)

Safety Data

• Hazardous Substances Data: 141899-12-9(Hazardous Substances Data)

Usage

Description

L-Homotyrosine hydrobromide is an off-white solid that is utilized in the pharmaceutical industry for the synthesis of various compounds, particularly in the preparation of azoles which serve as oral antidiabetic agents. L-Homotyrosine hydrobromide plays a significant role in the development of medications that help manage blood sugar levels in individuals with diabetes.

Uses

Used in Pharmaceutical Industry:
L-Homotyrosine hydrobromide is used as a key intermediate in the synthesis of azoles for the development of oral antidiabetic agents. These agents are crucial in the treatment of diabetes, as they help regulate blood sugar levels and improve the overall management of the condition.
Used in the Preparation of Azoles:
L-Homotyrosine hydrobromide is used as a chemical precursor for the production of azoles, which are essential in the creation of oral antidiabetic medications. These medications are designed to help patients with diabetes maintain healthy blood sugar levels, thus reducing the risk of complications associated with the disease.

InChI:InChI=1/C10H13NO3.BrH/c11-9(10(13)14)6-3-7-1-4-8(12)5-2-7;/h1-2,4-5,9,12H,3,6,11H2,(H,13,14);1H/t9-;/m0./s1

Upstream product

• 110936-12-4 N-(methylcarbamoyl)homotyrosine methyl ester 

Downstream Products

• 141806-16-8 O-(2,6-dichlorobenzyl)-L-homotyrosine 
• 198560-10-0 Fmoc-hTyrOH 
• 894807-26-2 (S)-2-Amino-4-(4-benzyloxy-phenyl)-butyric acid 
• 296774-52-2 Boc-hTyrOMe 
• 1417189-26-4 C₂₃H₂₆N₂O₄*ClH 
• 1417189-24-2 C₂₈H₃₄N₂O₆ 
• 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 
• 141806-17-9 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.