A Practical Method for Functionalized Peptide or Amide Bond Formation in Aqueous−Ethanol Media with EDC as Activator

Pu, Yangwei John; Vaid, Radhe K.; Boini, Sathish K.; Towsley, Robert W.; Doecke, Christopher W.; Mitchell, David

doi:10.1021/op800240d

Cited by 34 publications

(31 citation statements)

References 24 publications

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“…LY450139, BMS-708163, and GSM-2 were synthesized at Astellas Pharma, Inc. (Tsukuba, Japan), according to the literature (Pu et al, 2008;Gillman et al, 2010) or patent application (Garcia et al, 2007). The chemical structures of the drugs are shown in Figure 1.…”

Section: Methodsmentioning

confidence: 99%

Differential Effects between γ-Secretase Inhibitors and Modulators on Cognitive Function in Amyloid Precursor Protein-Transgenic and Nontransgenic Mice

Mitani

Yarimizu²,

Saita³

et al. 2012

J. Neurosci.

179

189

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␥-Secretase inhibitors (GSIs) reduce amyloid-␤ (A␤) peptides but inevitably increase the ␤-C-terminal fragment (␤-CTFSubchronic dosing with either GSI rather impaired normal cognition in 3-month-old Tg2576 mice, with no inhibition on the processing of other ␥-secretase substrates, such as Notch, N-cadherin, or EphA4, in the brain. LY450139 also impaired normal cognition in wild-type mice; however, the potency was 10-fold lower than that in Tg2576 mice, indicating an APP-dependent mechanism likely with ␤-CTF accumulation. Immunofluorescence studies revealed that the ␤-CTF accumulation was localized in the presynaptic terminals of the hippocampal stratum lucidum and dentate hilus, implying an effect on presynaptic function in the mossy fibers. In contrast, both acute and subchronic dosing with GSM-2 significantly ameliorated memory deficits in Tg2576 mice and did not affect normal cognition in wild-type mice. We demonstrated a clear difference between GSI and GSM in effects on functional consequences, providing new insights into strategies for developing these drugs against Alzheimer's disease.

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Section: Methodsmentioning

confidence: 99%

Differential Effects between γ-Secretase Inhibitors and Modulators on Cognitive Function in Amyloid Precursor Protein-Transgenic and Nontransgenic Mice

Mitani

Yarimizu²,

Saita³

et al. 2012

J. Neurosci.

179

189

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“…28 The synthetic steps leading to 16 demonstrated high yields for amide bond formation with various secondary amines in the presence of the unprotected primary alcohol, resulting from the judicious choice of coupling reagents. 29 In addition, the conversion of the primary hydroxy group to a carboxylic acid was efficient. These results demonstrate that the use of aminoalcohol instead of the corresponding -amino acid ester is an effective strategy for chain elongation of peptide frameworks.…”

Section: Please Do Not Adjust Marginsmentioning

confidence: 99%

Total synthesis and biological activity of dolastatin 16

et al. 2017

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The total synthesis of dolastatin 16, a macrocyclic depsipeptide first isolated from the sea hare Dolabella auricularia as a potential antineoplastic metabolite by Pettit et al., was achieved in a convergent manner. Dolastatin 16 was reported by Tan to exhibit strong antifouling activity, and thus shows promise for inhibiting the attachment of marine benthic organisms such as Amphibalanus amphitrite to ships and submerged artificial structures. Therefore, dolastatin 16 is a potential compound for a new, environmentally friendly antifouling material to replace banned tributyltin-based antifouling paints. The synthesis of dolastatin 16 involved the use of prolinol to prevent formation of a diketopiperazine composed of L-proline and N-methyl-D-valine during peptide coupling. This strategy for the elongation of peptide chains allowed the efficient and scalable synthesis of one segment, which was subsequently coupled with a second segment and cyclized to form the macrocyclic framework of dolastatin 16. The synthetic dolastatin 16 exhibited potent antifouling activity similar to that of natural dolastatin 16 toward cypris larvae of Amphibalanus amphitrite.

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“…To covalently bind 22 to the aminated silica surface the formation of amide bonds was brought about using 1-ethyl-3-(3-dimethylamionpropyl)carbodiimide (EDC) in combination with 1-hydroxybenzotriazole (HOBt) as coupling agent [21]. Tables 1-3 comprise the results of grafting initiator layers using 16 and 22, respectively, and of forming brushes from various monomers.…”

Section: Synthesis Of Double Startersmentioning

confidence: 99%

NMRP and ATRP Double Initiators for the Formation of Binary Polymer Brushes via Grafting-From Methods

Thiessen

Wolff

2011

Designed Monomers and Polymers

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New ATRP and NMRP initiator molecules were synthesized, which were grafted on silica wafer surfaces and served for initiating the formation of polymer brushes via the grafting-from method. Two of the new initiators bore ATRP and NMRP moieties in the same molecule. These double initiators were used to produce binary polymer brushes with switchable surface properties: styrene was first polymerized via ATRP at 40 • C and 4-vinylpyridine was polymerized thereafter at 110 • C via NMRP. The brushes achieved in this way exhibited smooth surfaces differing in the thickness of the brush layers by less than 10% (at different areas of the wafers) and could be switched from hydrophobic to hydrophilic and vice versa.

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A Practical Method for Functionalized Peptide or Amide Bond Formation in Aqueous−Ethanol Media with EDC as Activator

Cited by 34 publications

References 24 publications

Differential Effects between γ-Secretase Inhibitors and Modulators on Cognitive Function in Amyloid Precursor Protein-Transgenic and Nontransgenic Mice

Differential Effects between γ-Secretase Inhibitors and Modulators on Cognitive Function in Amyloid Precursor Protein-Transgenic and Nontransgenic Mice

Total synthesis and biological activity of dolastatin 16

NMRP and ATRP Double Initiators for the Formation of Binary Polymer Brushes via Grafting-From Methods

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