90508-28-4

Basic information

• Product Name: ALOC-ALA-OH DCHA
• Synonyms: N-ALLYLOXYCARBONYL-L-ALANINE DICYCLOHEXYLAMINE SALT;N-ALPHA-ALLYLOXYCARBONYL-ALANINE DICYCLOHEXYLAMINE SALT;ALLOC-L-ALANINE DICYCLOHEXYLAMINE SALT;ALLOC-ALA-OH DICYCLOHEXYLAMINE SALT;ALLYLOXYCARBONYL-L-ALANINE DICYCLOHEXYLAMMONIUM SALT;ALOC-ALANINE-OH DCHA;ALOC-ALA-OH DCHA;Aloc-Ala-OH
• CAS NO: 90508-28-4
• Molecular Formula: C₇H₁₁NO₄
• Molecular Weight: 354.48
• Mol File: 90508-28-4.mol
• Article Data: 9

Chemical Properties

• Melting Point: 139-142 °C
• Boiling Point: 324.2±35.0 °C(Predicted)
• Appearance: /
• Density: 1.182±0.06 g/cm3(Predicted)
• Storage Temp.: -15°C
• PKA: 3.98±0.10(Predicted)
• CAS DataBase Reference: ALOC-ALA-OH DCHA(CAS DataBase Reference)
• NIST Chemistry Reference: ALOC-ALA-OH DCHA(90508-28-4)
• EPA Substance Registry System: ALOC-ALA-OH DCHA(90508-28-4)

Safety Data

• WGK Germany: 3
• F: 10-23
• Hazardous Substances Data: 90508-28-4(Hazardous Substances Data)

Usage

Description

ALOC-ALA-OH DCHA, also known as (2S)-2-amino-3-(1H-1,2,3-triazol-1-yl)propanoic acid, is a chemical compound that serves as a key intermediate in the synthesis of various pharmaceutical agents. It is characterized by its unique structure, which includes an amino group, a triazole ring, and a carboxylic acid moiety. These functional groups enable ALOC-ALA-OH DCHA to participate in a wide range of chemical reactions and form stable conjugates with other molecules, making it a valuable building block in medicinal chemistry.

Uses

Used in Pharmaceutical Industry:
ALOC-ALA-OH DCHA is used as a key intermediate in the synthesis of pyrrolobenzodiazepine derivatives, which are known for their potent anticancer properties. These derivatives are particularly useful as antibody-drug conjugates (ADCs), a promising class of targeted cancer therapies. ADCs combine the selective targeting of monoclonal antibodies with the cytotoxic effects of chemotherapeutic agents, allowing for the precise delivery of these drugs to cancer cells while minimizing damage to healthy tissues.
In the preparation of pyrrolobenzodiazepine-based ADCs, ALOC-ALA-OH DCHA plays a crucial role in the formation of stable covalent bonds between the drug payload and the antibody. This ensures that the conjugate remains intact in the bloodstream and only releases the active drug once it has reached the tumor site, thereby maximizing therapeutic efficacy and minimizing side effects.
Furthermore, the versatility of ALOC-ALA-OH DCHA allows for the development of a variety of pyrrolobenzodiazepine-based ADCs with different mechanisms of action and targeting specificities. This enables the design of personalized cancer treatments tailored to the unique characteristics of individual tumors, ultimately improving patient outcomes and survival rates.

Upstream product

• 56-41-7 L-alanin 
• 115491-93-5 diallyl dicarbonate 
• 2937-50-0 Allyl chloroformate 
• 35661-39-3 N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine 
• 135544-68-2 N-(allyloxycarbonyloxy)succinimide 

Downstream Products

• 128369-70-0 (S)-methyl 2-(((allyloxy)carbonyl)amino)propanoate 
• 167423-69-0 {(S)-1-[(R)-1-(3-Allyloxy-phenyl)-2-(tert-butyl-dimethyl-silanyloxy)-ethylcarbamoyl]-ethyl}-carbamic acid allyl ester 
• 190207-36-4 (S)-2-[(S)-2-((S)-2-Allyloxycarbonylamino-propionylamino)-3-methyl-butyrylamino]-3-phenyl-propionic acid 3-methyl-but-2-enyl ester 
• 145147-59-7 Aloc-Ala-Phe-OtBu 
• 132402-82-5 (S)-1-((S)-2-{[2-((S)-1-Allyloxycarbonylamino-ethyl)-thiazole-4-carbonyl]-amino}-3-phenyl-propionyl)-pyrrolidine-2-carboxylic acid tert-butyl ester 
• 1151813-32-9 allyl (S)-1-((4R,5R)-4-methyl-5-phenyl-4,5-dihydrooxazol-2-yl)ethylcarbamate 
• 56-41-7 L-alanin 

Relevant articles and documents

A novel synthesis of oligonucleotide-peptide conjugates with a base- labile phosphate linker between the two components according to the allyl- protected phosphoramidite strategy

An efficient synthesis of base-labile nucleotide-peptide conjugates has been accomplished, in which the two components are directly linked between the terminal hydroxyl of a nucleotide and the hydroxyl of a serine or threonine residue of a peptide by a phosphodiester bond. This synthesis utilizes the phosphoramidite method with allyl for the phosphate linkages and the C-terminal of the peptide and allyloxycarbonyl for the nucleoside bases and the N-terminal of the peptide. In this synthesis, the removal of the allylic protecting groups and the detachment of the products was achieved under non-basic or mild basic conditions to bring about no conspicuous decomposition of the labile phosphate linker, and thus the target conjugates were obtained at a high purity and in high yields. (C) 2000 Elsevier Science Ltd.

PYRROLOBENZODIAZEPINE ANTIBODY CONJUGATES

The present disclosure relates generally to antibody-drug conjugates comprising pyrrolo[2, 1-c][1, 4]benzodiazepine (PBD) drug moieties. The present disclosure also relates to methods of using these conjugates, e.g., as therapeutics and/or diagnostics.

Desyl and phenacyl as versatile, photocatalytically cleavable protecting groups: A classic approach in a different (visible) light

A highly efficient, catalytic strategy for the deprotection of classical phenacyl (Pac) as well as desyl (Dsy) protection groups has been developed using visible light photoredox catalysis. The deliberate use of a neutral two-phase acetonitrile/water mixture with K3PO4 applying catalytic amounts of [Ru(bpy)3](PF6)2 in combination with ascorbic acid is the key to this truly catalytic deprotection of Pac- and Dsy-protected carboxylic acids. Our mild yet robust protocol allows for fast and selective liberation of the free carboxylic acids in very good to quantitative yields, while only low catalyst loadings (1 mol %) are required. Both Pac and Dsy, easily introduced from commercially available precursors, can be applied for the direct protection of carboxylic acids and amino acids, offering orthogonality to a great variety of other common protecting groups. We further demonstrate the general applicability and versatility of these formerly underrated protecting groups in combination with our catalytic cleavage conditions, as underscored by the gained high functional group tolerance. Moreover, this method could successfully be adapted to the requirements of solidphase synthesis. As a proof of principle for an efficient visible light, photocatalytic linker cleavage, a Boc-protected tripeptide was split off from commercially available brominated Wang resin.