N-Tetrahydrofuroyl-(l)-phenylalanine derivatives as potent VLA-4 antagonists

Yang, Gee-Gwo; Chang, Linda; Truong, Quang; Doherty, George; Magriotis, Plato Α.; Laszlo, Stephen E. de; Li, Bing; MacCoss, Malcolm; Kidambi, Usha; Egger, Linda A.; McCauley, Ermengilda; Riper, Gail Van; Mumford, Richard A.; Schmidt, John A.; Hagmann, William K.

doi:10.1016/s0960-894x(02)00210-x

Cited by 30 publications

(22 citation statements)

References 13 publications

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“…[194,195]. Highly potent analogues, for example, 120 and 121 ( Figure 18A), were obtained when encompassing a biarylic C-terminal residue.…”

Section: The Suzuki-miyaura Reaction As a Tool Towards Improved Biolomentioning

confidence: 99%

“…The groups of Hagmann and Yang described the optimization of sulfonylated dipeptide inhibitors with subnanomolar inhibitory activity for integrin VLA-4 as illustrated by compound 119. [194,195]. Highly potent analogues, for example, 120 and 121 ( Figure 18A), were obtained when encompassing a biarylic C-terminal residue.…”

Section: The Suzuki-miyaura Reaction As a Tool Towards Improved Biolomentioning

confidence: 99%

“…Modification of the substituents on the distal ring of biphenylalanine altered the availability, half-life and clearance rate of the dipeptide ligands. Synthesis of these ligands was carried out by Suzuki-Miyaura reaction on the protected triflated tyrosine [194] or halogenated phenylalanine [195] with Pd(PPh3)4 in toluene and the corresponding boronic acids to yield 120 and 121.…”

Section: The Suzuki-miyaura Reaction As a Tool Towards Improved Biolomentioning

confidence: 99%

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The Suzuki–Miyaura Cross-Coupling as a Versatile Tool for Peptide Diversification and Cyclization

et al. 2017

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Abstract:The (site-selective) derivatization of amino acids and peptides represents an attractive field with potential applications in the establishment of structure-activity relationships and labeling of bioactive compounds. In this respect, bioorthogonal cross-coupling reactions provide valuable means for ready access to peptide analogues with diversified structure and function. Due to the complex and chiral nature of peptides, mild reaction conditions are preferred; hence, a suitable cross-coupling reaction is required for the chemical modification of these challenging substrates. The Suzuki reaction, involving organoboron species, is appropriate given the stability and environmentally benign nature of these reactants and their amenability to be applied in (partial) aqueous reaction conditions, an expected requirement upon the derivatization of peptides. Concerning the halogenated reaction partner, residues bearing halogen moieties can either be introduced directly as halogenated amino acids during solid-phase peptide synthesis (SPPS) or genetically encoded into larger proteins. A reversed approach building in boron in the peptidic backbone is also possible. Furthermore, based on this complementarity, cyclic peptides can be prepared by halogenation, and borylation of two amino acid side chains present within the same peptidic substrate. Here, the Suzuki-Miyaura reaction is a tool to induce the desired cyclization. In this review, we discuss diverse amino acid and peptide-based applications explored by means of this extremely versatile cross-coupling reaction. With the advent of peptide-based drugs, versatile bioorthogonal conversions on these substrates have become highly valuable.

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“…[194,195]. Highly potent analogues, for example, 120 and 121 ( Figure 18A), were obtained when encompassing a biarylic C-terminal residue.…”

Section: The Suzuki-miyaura Reaction As a Tool Towards Improved Biolomentioning

confidence: 99%

Section: The Suzuki-miyaura Reaction As a Tool Towards Improved Biolomentioning

confidence: 99%

Section: The Suzuki-miyaura Reaction As a Tool Towards Improved Biolomentioning

confidence: 99%

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The Suzuki–Miyaura Cross-Coupling as a Versatile Tool for Peptide Diversification and Cyclization

et al. 2017

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“…It turned out that only 5 mol-% of the commercial Pd 0 source tetrakis(triphenylphosphine)palladium [Pd(PPh 3 ) 4 ] was necessary to give the Boc-b 3 hPhe-OMe derivatives 6a -6f in yields of 82 -97% (Scheme 2). Such enantiomerically pure protected b 3 -homoamino acids have previously been obtained by employing organozinc reagents [13], which require the preparation and handling of sensitive organometallic reagents.…”

Section: Suzuki Cross-coupling Reaction In Solutionmentioning

confidence: 99%

“…-The Suzuki-Miyaura cross-coupling reaction is a powerful synthetic tool for C,C-coupling reactions of borono derivatives with aryl or vinyl halides or triflates 5 ), as the reaction is unaffected by the presence of H 2 O, tolerates a broad range of functional groups, proceeds regio-and stereoselectively in good yields, and nontoxic inorganic side-products are easily removed. The reaction has been used with (4-borono)-[2], (4-bromo)- [3], and (4-iodo)phenylalanine [4] [5], serine-derived alkylboronic acids [6], and tyrosine triflates [3] [7] for the preparation of phenylalanine derivatives, which are modified in the 4-aryl position. These unnatural amino acids have been incorporated into small peptides to increase both their pharmacological potential and metabolic stability [8].…”

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confidence: 99%

Synthesis ofβ3-Homophenylalanine-Derived Amino Acids and Peptides bySuzuki Coupling in Solution and on Solid Support

Limbach

Löweneck

Schreiber

et al. 2006

HCA

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and, to a certain extent, also mixed a,b-peptides, are resistant to degradation by a variety of proteolytic enzymes that rapidly degrade natural a-peptides. This is one of many characteristics that make b-peptides an attractive class of compounds for drug-discovery studies. On the other hand, modern organometallic reactions such as the Suzuki-Miyaura cross-coupling have become standard tools in industry laboratories to derivatize side chains of a-peptidic compounds to build up libraries of unnatural peptides. Combining both features, we prepared (4-bromo)-b 3 -homophenylalanine derivatives 3 -5 and 12 as precursors for Suzuki-Miyaura couplings. From these bromo compounds, we synthesized biarylsubstituted b-homoamino acids 6, and analogs 13 and 15 of the anti-AIDS drug Saquinavir.Introduction. -The Suzuki-Miyaura cross-coupling reaction is a powerful synthetic tool for C,C-coupling reactions of borono derivatives with aryl or vinyl halides or triflates 5 ), as the reaction is unaffected by the presence of H 2 O, tolerates a broad range of functional groups, proceeds regio-and stereoselectively in good yields, and nontoxic inorganic side-products are easily removed. The reaction has been used with (4-borono)-[2], (4-bromo)- [3], and (4-iodo)phenylalanine [4] [5], serine-derived alkylboronic acids [6], and tyrosine triflates [3] [7] for the preparation of phenylalanine derivatives, which are modified in the 4-aryl position. These unnatural amino acids have been incorporated into small peptides to increase both their pharmacological potential and metabolic stability [8].

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Copper‐Catalyzed Amination of Aryl and Alkenyl Electrophiles

2014

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The copper‐catalyzed arylation and vinylation of nitrogen nucleophiles is a highly versatile method for the construction of sp 2 C–N bonds. Copper‐catalyzed C–N bond formation has an extensive history and the field has been reinvigorated with the development of ligand‐promoted catalyst systems that provide general and effective reactions under relatively mild conditions. Copper promotes arylation and vinylation of a wide range of nitrogen nucleophiles, including amines, nitrogen heterocycles, and amide derivatives. The reactivity profile is complementary to that of palladium and often offers orthogonal chemoselectivity. This chapter presents a thorough overview of the copper‐catalyzed coupling of aryl and vinyl halides with nitrogen nucleophiles. Current understanding of the mechanism of this process is presented along with a detailed overview of the scope and limitations of this reaction along with optimal reaction conditions for the coupling of various nitrogen nucleophile classes.

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N-Tetrahydrofuroyl-(l)-phenylalanine derivatives as potent VLA-4 antagonists

Cited by 30 publications

References 13 publications

The Suzuki–Miyaura Cross-Coupling as a Versatile Tool for Peptide Diversification and Cyclization

The Suzuki–Miyaura Cross-Coupling as a Versatile Tool for Peptide Diversification and Cyclization

Synthesis ofβ3-Homophenylalanine-Derived Amino Acids and Peptides bySuzuki Coupling in Solution and on Solid Support

Copper‐Catalyzed Amination of Aryl and Alkenyl Electrophiles

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