Synthesis of 4,4-Disubstituted 2-Aminocyclopentanecarboxylic Acid Derivatives and Their Incorporation into 12-Helical β-Peptides

Peelen, Timothy J.; Chi, Young‐In; English, Emily P.; Gellman, Samuel H.

doi:10.1021/ol0483293

Cited by 24 publications

(16 citation statements)

References 27 publications

(15 reference statements)

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“…The oligomers of such non-protein-derived amino acids have been found to fold to 2.6 12 -helices in the crystalline state, as well as in solution ( Figure 5). [22][23][24][25][26][27][28][29] With b-peptides consisting of homologated proteinogenic amino acid residues, the 12-helix has not been detected experimentally, although molecular dynamics (MD) simulations and ab initio calculations suggest its existence (vide infra). The oligopeptides from cis-2-ACPC adopt a sheet-like structure.…”

Section: 454749mentioning

confidence: 99%

Helices and other secondary structures of β‐ and γ‐peptides

Seebàch

Hook

Glättli³

2005

Biopolymers

321

212

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The principal secondary structural motifs adopted by peptides assembled from beta-amino acid units are discussed: the 14-, 12-, 10-, 12/10-, and 8-helices, as well as the hairpin turn, extended structures, stacks, and sheets. Features that promote a particular folding propensity are outlined and illustrated by structures determined in solution (NMR) and in the solid-state (x-ray). The N-C(beta)-C(alpha)-CO dihedral angles from molecular dynamics simulations, which are indicative of a particular secondary structure, are presented. A brief description of a helix and a turn of gamma-peptides is also given.

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Section: 454749mentioning

confidence: 99%

Helices and other secondary structures of β‐ and γ‐peptides

Seebàch

Hook

Glättli³

2005

Biopolymers

321

212

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“…Several attempts have been made as regards modified the alicyclic b-amino acids trans-3-aminopyrrolidine-4-carboxylic acid and nipecotic acid, where no extra protection is necessary, 3-aminomethyl-ACPC, where the aminomethyl function is protected by Boc while the b-amino groups holds an Fmoc function, 29 and 4,4-disubstituted-ACPC derivatives bearing a tert-butyl ether and ester protection. 30 The major problem is usually the preparation of the appropriately protected building block; its incorporation is generally less problematic. The protection of the amino and hydroxy functions in the side-chain has been more or less solved, but the protection of other interesting functional groups such as guanidine or thiol has not yet been reported.…”

Section: Peptide Synthesesmentioning

confidence: 99%

Application of alicyclic β-amino acids in peptide chemistry

2006

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The self-organizing beta-peptides have attracted considerable interest in the fields of foldamer chemistry and biochemistry. These compounds exhibit various stable secondary structure motifs that can be exploited to construct biologically active substances and nanostructured tertiary structures. The secondary structures can be controlled via the beta-amino acid sequence, and cyclic beta-amino acid residues play a crucial role in the design. The most important procedures for the preparation of cyclic beta-amino acid monomers and peptides are discussed in this tutorial review. Besides the secondary structure design principles, the methods of folded structure detection are surveyed.

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“…6 Gellman et al applied this method to prepare enantiomerically pure 4,4-disubstituted derivatives of trans-β-aminocyclopentanecarboxylic acids. 7 The 4,4-disubstituted β-keto esters were reacted with (R)-α-methylbenzylamine and the resulting enamines were reduced with NaCNBH 3 . The diastereomeric mixture of trans-amino esters was separated by chromatography, followed by transformation to the corresponding disubstituted cyclic β-amino acids 34−37 ( Figure 5).…”

Section: I−smentioning

confidence: 99%

Synthesis of Carbocyclic and Heterocyclic β-Aminocarboxylic Acids

2013

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Introduction 1116 2. Carbocyclic β-Amino Acids 1118 2.1. Syntheses of Five-or Six-Membered Carbocyclic β-Amino Acids 1118 2.1.1. Carbocyclic β-Amino Acids from β-Keto Esters 1119 2.1.2. Carbocyclic β-Amino Acids by Metathesis 1119 2.1.3. Carbocyclic β-Amino Acids by Amino Group Conjugate Addition 1122 2.1.4. Carbocyclic β-Amino Acids by Cycloaddition 1124 2.1.5. Carbocyclic β-Amino Acids by Desymmetrization of meso-Anhydrides 1124 2.1.6. Carbocyclic β-Amino Acids from Natural Sources 1125 2.1.7. Miscellaneous 1127 2.2. Syntheses of Small-Ring Carbocyclic β-Amino Acids 1128 2.3. Syntheses of Carbocyclic β-Amino Acids with Larger Ring Systems 1129 2.4. Synthesis of Functionalized Carbocyclic β-Amino Acids 1131 2.4.1. Syntheses of Functionalized Cyclic β-Amino Acids by C−C Double Bond Functionalization 1131 2.4.2. Several Relevant Routes to Functionalized Cyclic β-Amino Acids Other Than Functionalization of the Ring C−C Double Bond 1137 3. Cyclic β-Amino Acids with a Heteroatom in the Ring 1137 3.1. Syntheses of Cyclic β-Amino Acids with a N Atom in the Ring 1138 3.1.1. Three-and Four-Membered N-Containing Cyclic β-Amino Acids 1138 3.1.2. Five-Membered N-Containing Cyclic β-Amino Acids 1138 3.1.3. Six-Membered N-Containing Cyclic β-Amino Acids 1145 3.1.4. N-Containing Cyclic β-Amino Acids with Larger Ring Systems 1148 3.2. Syntheses of Cyclic β-Amino Acids with an O Atom in the Ring 1148 3.2.1. Four-Membered O-Containing Cyclic β-Amino Acids 1148 3.2.2. Five-Membered O-Containing Cyclic β-Amino Acids 1149 3.2.3. Six-Membered O-Containing Cyclic β-Amino Acids 1155 3.3. Cyclic β-Amino Acids with Other Heteroatoms in the Ring 1159 4. Some Relevant Biological Properties of Cyclic β-Amino Acids 1160 4.1. Cyclic β-Amino Acids Possessing Antifungal or Antibacterial Properties 1160 4.2. Antiviral Cyclic β-Amino Acids 1162 4.3. Cyclic β-Amino Acids with Antitumoral Properties 1162 4.4. Cyclic β-Amino Acids with Cardioprotective

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Synthesis of 4,4-Disubstituted 2-Aminocyclopentanecarboxylic Acid Derivatives and Their Incorporation into 12-Helical β-Peptides

Cited by 24 publications

References 27 publications

Helices and other secondary structures of β‐ and γ‐peptides

Helices and other secondary structures of β‐ and γ‐peptides

Application of alicyclic β-amino acids in peptide chemistry

Synthesis of Carbocyclic and Heterocyclic β-Aminocarboxylic Acids

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