[4] Standard Fmoc protocols

Wellings, Donald A.; Atherton, Eric

doi:10.1016/s0076-6879(97)89043-x

Cited by 260 publications

(246 citation statements)

References 35 publications

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Section: )mentioning

confidence: 99%

“…23 We followed the established Fmoc protocol in which C-terminal N-Fmoc-protected aminoacid is loaded as HMPA ester through a N,N´-diisopropylcarbodiimide (DIPCDI, 22)-mediated coupling in the presence of catalytic DMAP (23) carried out twice. 23 Fmoc deprotection of the bound amino groups was induced with piperidine. 23 All subsequent N-Fmoc-protected aminoacids were incorporated by means of TBTU (24)-mediated couplings in the presence of DIPEA (25) followed by deprotection with piperidine, 26.…”

Section: )mentioning

confidence: 99%

“…23 Fmoc deprotection of the bound amino groups was induced with piperidine. 23 All subsequent N-Fmoc-protected aminoacids were incorporated by means of TBTU (24)-mediated couplings in the presence of DIPEA (25) followed by deprotection with piperidine, 26. DMF was used as solvent throughout these transformations.…”

Section: )mentioning

confidence: 99%

“…Ninhydrin (Kaiser) test of a small sample of resin resulted negative at this stage. 23 Finally, the resin was washed consecutively with DMF (10 x 30 ml) and diethyl ether (10 x 30 ml) and dried overnight at 40 o C under vacuum. …”

Section: Synthesis Of Slurps-hmpa and Pdma-hmpa Resins (General Procementioning

confidence: 99%

“…[20][21][22][23] We will discuss the synthesis of the aminofunctional SLURPS first, followed by linker conjugation, as this has not been reported before, followed by our SPPS of Leu-enkephalin.…”

Section: Introductionmentioning

confidence: 99%

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Novel Non-PEG Derived Polyethers as Solid Supports. 2. Solid-Phase Synthesis Studies

et al. 2007

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Novel non-PEG derived polyether resins, coined SLURPS (Superior Liquid Uptake Resins forPolymer-supported Synthesis), were studied for their performance in solid-phase synthesis. Novel amino functional resins, SLURPS-NH 2 , were prepared with a loading of up to 8.5 mmol/g and employed successfully in the solid-phase synthesis of Leu-Enkephalin. The peptide was obtained with the same 2 purity when compared to its synthesis with commercial standard poly(dimethyl acrylamide) resins.Furthermore we show loading and cleavage of aromatic carboxylic acids in excellent yield. The advantageous solvent compatibility of our support was demonstrated through the biphasic dihydroxylation of alkenes with OsO 4 in t-BuOH/water mixtures producing bound 1,2-diols and synthesis and removal of a bound oxime using ethanol/water mixtures both in excellent yields. Reactions were easily monitored by gel-phase NMR and FTIR These results show that SLURPS are very well suited for organic transformations using highly polar solvent mixtures and reagents and this at much higher loading levels than standard amphiphilic resins of similar solvent compatibility. Graphical Abstract:O OH SLURPS

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Section: )mentioning

confidence: 99%

Section: )mentioning

confidence: 99%

Section: )mentioning

confidence: 99%

Section: Synthesis Of Slurps-hmpa and Pdma-hmpa Resins (General Procementioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Novel Non-PEG Derived Polyethers as Solid Supports. 2. Solid-Phase Synthesis Studies

et al. 2007

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An examination of the steric effects of 5-tert-butylproline on the conformation of polyproline and the cooperative nature of type II to type I helical interconversion

Beausoleil

Lubell

2000

Biopolymers

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The influence of steric effects on the helical geometry and the interconversion of type II to type I polyproline in water was examined by the synthesis and analysis of proline dimers and hexamers containing up to three (2S,5R)‐5‐tert‐butylproline residues. In the dimers, the bulky 5‐tert‐butyl substituent was found to exert a significant influence on the local prolyl amide geometry such that the predominant trans‐isomer in N‐(acetyl)prolyl‐prolinamide (1) was converted to 63% cis isomer in N‐(acetyl)prolyl‐5‐tert‐butylprolinamide (2) as measured by 1H‐nmr spectroscopy. Similarly, the presence of a 5‐tert‐butyl group on the C‐terminal residue in the polyproline hexamer Ac–Pro5–t‐BuPro–NH2 (4) produced a local 5‐tert‐butylprolyl amide population containing 61% cis isomer in water. In spite of the presence of a local prolyl cis amide geometry, the downstream prolyl amides in 4 remained in the trans isomer as determined by NOESY spectroscopy. Conformational analysis by 13C‐nmr and CD spectroscopy indicated that Ac–Pro6–NH2 (3) adopted the all‐trans amide polyproline type II helix in water. As the amount of 5‐tert‐butylproline increased from one to three residues in hexamers 4–6, a gradual destabilization of the polyproline type II helical geometry was observed by CD spectroscopy in water; however, no spectrum was obtained, indicative of a complete conversion to a polyproline type I helix. The implications of these results are discussed with respect to the previously proposed theoretical mechanisms for the helical interconversion of polyproline, which has been suggested to occur by either a cooperative C‐ to N‐terminal isomerization of the prolyl amide bonds or via a conformational intermediate composed of dispersed sequences of prolyl amide cis and trans isomers. © 2000 John Wiley & Sons, Inc. Biopoly 53: 249–256, 2000

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Generation of Peptide MHC Class I Monomers and Multimers Through Ligand Exchange

et al. 2009

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The recognition of defined antigen-MHC complexes by antigen-specific T cells forms the molecular basis of T cell immunity. It has been shown that fluorescently labeled recombinant MHC tetramers can be utilized to detect antigen-specific T cells by flow cytometry. Since this first description, MHC tetramers and other types of MHC multimers have become a core tool to monitor the development of disease- and therapy-induced antigen-specific T cell responses both in humans and in animal model systems. This unit describes a set of protocols that transform classical MHC multimer technology into a high-throughput platform, allowing one to produce large collections of MHC class I molecules charged with different peptides. This technology is based on the development of conditional MHC ligands that can be triggered to self-destruct while in the MHC-bound state.

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[4] Standard Fmoc protocols

Cited by 260 publications

References 35 publications

Novel Non-PEG Derived Polyethers as Solid Supports. 2. Solid-Phase Synthesis Studies

Novel Non-PEG Derived Polyethers as Solid Supports. 2. Solid-Phase Synthesis Studies

An examination of the steric effects of 5-tert-butylproline on the conformation of polyproline and the cooperative nature of type II to type I helical interconversion

Generation of Peptide MHC Class I Monomers and Multimers Through Ligand Exchange

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