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Usage

Uses

BOC-D-DAP(FMOC)-OH is used as a pharmaceutical intermediate for the synthesis of various drugs and compounds. Its application in the pharmaceutical industry is primarily due to its ability to serve as a building block for the development of new medications.
Used in Pharmaceutical Industry:
BOC-D-DAP(FMOC)-OH is used as a key component in the synthesis of two ligands, with peptide or PEG linkers targeting the μ-opioid receptor (MOR) or the δ-opioid receptor (DOR). These ligands are crucial in the development of medications aimed at treating pain and addiction, as they can modulate the activity of these receptors, potentially leading to more effective therapies.

Upstream product

• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 73259-81-1 (R)-2-tert-butoxycarbonyl-3-aminopropionic acid 
• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 
• 7536-55-2 N-t-butyloxycarbonyl-D-asparagine 
• 124730-06-9 (S)-3-Benzylamino-2-tert-butoxycarbonylamino-propionic acid 
• 177740-14-6 N-[(1,1-dimethylethoxy)carbonyl]-L-asparagine 
• 7536-55-2 N-tert-butyloxycarbonylasparagine 
• 76387-70-7 (S)-3-amino-2-tert-butoxycarbonylaminopropionic acid 

Downstream Products

• 134653-36-4 Boc-Dap(Fmoc)-Ala p-nitrobenzyl ester 
• 753029-55-9 5-[(2R,3S)-3-((S)-2-{(S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(9H-fluoren-9-ylmethoxycarbonylamino)-propionylamino]-3-methyl-butyrylamino}-4-methyl-pentanoylamino)-2-hydroxy-4-phenyl-butyrylamino]-isophthalic acid dimethyl ester 

Relevant academic research and scientific papers

2,3-Diaminopropanols obtained from D-serine as intermediates in the synthesis of protected 2,3-L-diaminopropanoic acid (L-DAP) methyl esters

A synthetic strategy for the preparation of two orthogonally protected methyl esters of the non-proteinogenic amino acid 2,3-l-diaminopropanoic acid (l-Dap) was developed. In these structures, the base-labile protecting group 9-fluorenylmethyloxycarbonyl (Fmoc) was paired to the p-toluensulfonyl (tosyl, Ts) or acid-labile tert-butyloxycarbonyl (Boc) moieties. The synthetic approach to protected l-Dap methyl esters uses appropriately masked 2,3-diaminopropanols, which are obtained via reductive amination of an aldehyde prepared from the commercial amino acid Nα-Fmoc-O-tert-butyl-d-serine, used as the starting material. Reductive amination is carried out with primary amines and sulfonamides, and the process is assisted by the Lewis acid Ti(OiPr)4. The required carboxyl group is installed by oxidizing the alcoholic function of 2,3-diaminopropanols bearing the tosyl or benzyl protecting group on the 3-NH2 site. The procedure can easily be applied using the crude product obtained after each step, minimizing the need for chromatographic purifications. Chirality of the carbon atom of the starting d-serine template is preserved throughout all synthetic steps.

COMPOUNDS AND USES THEREOF

The present disclosure features compounds useful for the treatment of BAF complex-related disorders.

Fluorophore ATCUN complexes: Combining agent and probe for oxidative DNA cleavage

DNA can be oxidatively cleaved by copper complexes of the ATCUN peptide (amino terminal Cu(II)- and Ni(II)-binding motif). In order to investigate the fate of the metal ion throughout this process, we have exploited quenching/dequenching effects of conjugated fluorophores.

Iridium-catalyzed asymmetric allylic amination with polar amines: Access to building blocks with lead-like molecular properties

The combination of an air-stable iridium catalyst and the dipolar aprotic solvent dimethyl sulfoxide (DMSO) allowed, for the first time, the systematic exploitation of highly polar, functionalized amines in asymmetric allylic substitutions: low molecular

Novel inhibitors of procollagen C-terminal proteinase. Part 1: Diamino acid hydroxamates

The parallel synthesis of novel inhibitors of procollagen C-terminal proteinase is described. The synthetic strategy allowed for the facile synthesis of a large number of side-chain diversified diamino acid hydroxamates, of which the D-diaminopropionic acid derivatives were shown to be single digit nanomolar PCP inhibitors.

Diaminopropionic acid derivatives

A compound of formula 1a which is useful for treating reperfusion injury, and salts, prodrugs, and related compounds.

Synthesis and study of peptides with semirigid i and i+7 side-chain bridges designed for α-helix stabilization

A search for conformational constraints on the peptide α-helical conformation indicated that para-substituted amino acid derivatives of a benzene ring might be suitable for linking pairs of side chains that are separated by two turns of the helix. A 14-residue synthetic, amphiphilic α-helical peptide model system has been used to study the helix stabilizing effects of a series of four such bridges having constitutionally isomeric structures. These bridges were used to link positions 3 and 10 of the model peptides. The peptides were synthesized in good yield by standard solid-phase methods, including cyclization on the solid support. They were then studied for their solution conformations and melting behavior by circular dichroism (CD) spectropolarimetry, and for their elution behavior on reversed-phase HPLC columns. In aqueous solution and in 50% (v/v) trifluoroethanol, the most effective bridge for helix stabilization consisted of a 4-(aminomethyl)phenylacetic acid residue (AMPA) linked by amide bonds to the side chain functional groups of a (S)-2,3-diaminopropionic acid residue (Dap) in position 3 of the model peptide and an aspartic acid residue in position 10. This Dap3(AMPA), Asp10 bridge was about as effective as two Lys(i), Asp(i+4) lactam bridges incorporated linking residues 3 and 7, and 10 and 14, in the same model peptide sequence. This suggests that it is worth about 1kcal/mol of helix stabilization energy. Copyright (C) 1999 Elsevier Science Ltd.

Studies related to the absolute configuration of cyclocinamide A: Total synthesis of 4(R),11(R)-cyclocinamide A

Coupling of the fluorenylmethyl ester 3 (R = Fm) of (S)-5- bromotryptophan with N(α)-BOC-(S)-asn-O-benzoyl-(R)-ise 9 gave rise to tripeptide 10. Cleavage of the BOC group in 10 followed by coupling with N(α)-BOC-N(β)-Fmoc-(R)-2,3-diaminopropanoic acid afforded tetrapeptide 11 which was transformed into cyclic peptide 12. Cleavage of the BOC in 12 followed by coupling with the glycine derived side chain 14 gave rise, after removal of the benzoyl group to 4(R),11(R)-cyclocinamide A(2) which was not identical to natural cyclocinamide A(1), suggesting that 1 possesses the 4(S),7(S),11(S),14(S) configuration.

Synthesis of Peptides Containing Unnatural, Metal-Ligating Residues: Aminodiacetic Acid as a Peptide Side Chain

Peptides possessing a pair of residues separated by one turn in the α-helical conformation and potentially capable of ligating a single metal ion in aqueous solution were designed.It was predicted that the resulting cross-link would shift toward α-helix the random coil/α-helix equilibrium.The syntheses of 10 peptides Ac-AdalAlamAdal(Ala4GluLys)n-NH2 where Adal is an L-α-amino acid residue with an aminodiacetic acid bearing side chain, -(CH2)lN(CH2CO2H)2 (with values of l, m and n as follows: 1, 2, 3 (1); 1, 3, 1 (2a); 1, 3, 2 (2b); 1, 3, 3 (2c); 2, 2, 3 (3); 2, 3, 3 (4); 3, 2 ,3 (5); 3, 3, 3 (6); 4, 2, 3 (7); 4, 3, 3 (8) are described using Boc chemistry on p-methylbenzhydrylamine resin.The aminodiacetic acid bearing residues were incorporated with side chains protected as the dibenzyl esters.To avoid side reactions, residues Adal for l=1 and 2 were incorporated by a block approach.Peptide structures were confirmed by observation of the predicted parent ions in the FAB MS.The circular dichroism spectra of several of these peptides that possess a pair of metal-ligating residues separated by two or three intervening residues have previously been shown to undergo changes on addition of metal ions consistent with appreciable enhancement of helix content.