90508-28-4

Usage

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

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

Relevant academic research and scientific papers

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.

CALPAIN MODULATORS AND THERAPEUTIC USES THEREOF BACKGROUND

Disclosed herein are small molecule calpain modulators, pharmaceutical compositions, preparation methods and their use as therapeutic agents. The therapeutic agents can be used for treating fibrotic disease or a resulting secondary disease state or condition. The small molecules can inhibit calpain through contact with CAPN1, CAPN2, and/or CAPN9 enzymes.

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.

Total Synthesis of the Post-translationally Modified Polyazole Peptide Antibiotic Goadsporin

The structurally unique polyazole antibiotic goadsporin contains six heteroaromatic oxazole and thiazole rings integrated into a linear array of amino acids that also contains two dehydroalanine residues. An efficient total synthesis of goadsporin is repo

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.

Synthesis of a PNA-encoded cysteine protease inhibitor library

Peptide nucleic acids (PNAs) have been used to encode a combinatorial library whereby each compound is labeled with a PNA tag which reflects its synthetic history and localizes the compound upon hybridization to an oligonucleotide array. We report herein

New polymer-supported allyloxycarbonyl (Alloc) and propargyloxycarbonyl (Proc) amino-protecting reagents

New polymer-supported reagents, Alloc-P-OSu and Proc-P-OSu, have been prepared from a polymeric N-hydroxysuccinimide (P-HOSu), and used as solid-supported reagents for the allyloxycarbonyl (Alloc) and propargyloxycarbonyl (Proc) protection of the amino group. These new polymeric reagents are safe and stable, the residual P-HOSu generated after the protection reaction can be easily separated by simple filtration and reused.

Palladium-catalyzed transprotection of allyloxycarbonyl-protected amines: Efficient one-pot formation of amides and dipeptides

The synthetic utility of the N-(allyloxycarbonyl) (Alloc) substituent in α-amino acid derivatives is substantially extended beyond its well-known function as an amine protecting group. When the palladium-catalyzed deprotection is carried out by using tributyltin hydride as nucleophile (the Guibe method) in the presence of an active acylating agent a new acyl group is introduced on nitrogen. Successful acylating agents include carboxylic acid anhydrides, acid chlorides, and activated esters. A useful example of this methodology is the removal of the Alloc group in the presence of tert-butyl dicarbonate, which in essence amounts to a 'transprotection' to a Boc-protected α-amino acid derivative. More importantly, the use of activated N-protected α-amino ester derivatives (e.g., pentafluorophenyl esters) leads to dipeptides. This new method for peptide coupling proceeds very fast under mild conditions, in good to excellent yields, and without noticeable racemization.

DIALLYL DICARBONATE. A CONVENIENT REAGENT FOR THE SYNTHESIS OF ALLYL CARBAMATES

Diallyldicarbonate was prepared and used for the amino protection of various compounds including amino acids, amino sugars and nucleosides.