Solid phase sequential 1,3-dipolar cycloaddition–Pictet–Spengler reactions

Döndaş, H. Ali; Grigg, Ronald; MacLachlan, William S.; MacPherson, David T.; Markandu, Jasothara; Sridharan, Visuvanathar; Suganthan, Selveratnam

doi:10.1016/s0040-4039(99)02183-8

Cited by 43 publications

(19 citation statements)

References 7 publications

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“…Cleavage of the derivatized peptides from the Merrifield resin was accomplished using a solution of Et 3 N/THF/MeOH (1/2/2, vol/vol/vol) according to the modified procedure described by Dondas et al [22]. A sample of the peptidyl resin (5 mg) was placed in a standard CEM glass microwave vial and swelled in THF (0.5 mL) for 1 h. Then the solution of the Et 3 N/THF/MeOH (1 mL) was added.…”

Section: Methodsmentioning

confidence: 99%

Gas-Phase Fragmentation of Oligoproline Peptide Ions Lacking Easily Mobilizable Protons

Wieczorek

Kluczyk

Stefanowicz

et al. 2013

J. Am. Soc. Mass Spectrom.

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The fragmentation of peptides containing quaternary ammonium group, but lacking easily mobilizable protons, was examined with the aid of deuterium-labeled analogs and quantum-chemical modeling. The fragmentation of oligoproline containing quaternary ammonium group involves the mobilization of hydrogens localized at α- and γ- or δ-carbon atoms in the pyrrolidine ring of proline. The study of the dissociation pattern highlights the unusual proline residue behavior during MS/MS experiments of peptides.Electronic supplementary materialThe online version of this article (doi:10.1007/s13361-013-0585-1) contains supplementary material, which is available to authorized users.

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Section: Methodsmentioning

confidence: 99%

Gas-Phase Fragmentation of Oligoproline Peptide Ions Lacking Easily Mobilizable Protons

Wieczorek

Kluczyk

Stefanowicz

et al. 2013

J. Am. Soc. Mass Spectrom.

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“…18 The subsequent reaction of the dipolarophile with imines produced ester-linked cycloadducts that were cleaved from the resin as methyl esters by transesterification. 18 The subsequent reaction of the dipolarophile with imines produced ester-linked cycloadducts that were cleaved from the resin as methyl esters by transesterification.…”

Section: Solid-phase Synthesis Of Pyrrolidines Pyrrolines and Pyrrolesmentioning

confidence: 99%

Recent Advances in Solid‐Phase 1,3‐Dipolar Cycloaddition Reactions

Harju

Yli‐Kauhaluoma

2011

Solid‐Phase Organic Synthesis

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“…These efforts have led to successful protocol for a silver-catalyzed azomethine ylide cycloaddition and a subsequent rhodium-catalyzed [2þ2þ2] cycloisomerization, 69 as well as a tandem Heck-azomethine ylide cycloaddition. 73 After the Pictet-Spengler step the products were cleaved of the solid phase using TFA. For example, azomethine cycloaddition followed by a Pictet-Spengler cyclization gives access to a variety of bridged tri-, tetra-, penta-, 71 and hexacyclic 72 indole derivatives.…”

Section: Selected Applications and Extensions Of Azomethine [3+2] Cycmentioning

confidence: 99%