Solid-Phase Methods for the Microwave-Assisted Synthesis of Heterocycles

Erdélyi, Máté

doi:10.1007/7081_001

Cited by 14 publications

(4 citation statements)

References 161 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The 4-thiazolidinone ring system comprises a large number of biologically active compounds that have been evaluated for their anticonvulsant [7,8], antidiarrheal [9], antiplatelet activating [10], antimicrobial [3,10,11], anti-HIV [12][13][14][15], and anticancer [16][17][18] activities. Several methods for the stereoselective synthesis of thiazolidin-4-ones are available in the literature [19][20][21][22][23][24][25][26][27][28][29].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of bis-thiazolidin-4-ones from N,N,N″-(1,ω-alkanediyl)bis(N″-organylthiourea) derivatives

Hassan

El‐Shaieb

El-Aal

et al. 2015

Zeitschrift Für Naturforschung B

View full text Add to dashboard Cite

Section: Introductionmentioning

confidence: 99%

Synthesis of bis-thiazolidin-4-ones from N,N,N″-(1,ω-alkanediyl)bis(N″-organylthiourea) derivatives

Hassan

El‐Shaieb

El-Aal

et al. 2015

Zeitschrift Für Naturforschung B

View full text Add to dashboard Cite

“…Since the first report on application of the microwave irradiation in SPPS, a number of reports have been published showing advantages of using that technology in peptide synthesis . Microwave irradiation was applied to loading of the resin , coupling of amino acids, cleavage of peptides from a solid support and specific peptide‐bond cleavage . The microwave‐assisted methods of cleavage of peptides from solid supports described in the literature are concerned with cases when the peptide is cleaved from the resin simultaneously with the side chain deprotection in a one‐step procedure.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, biological activity and conformational analysis of head‐to‐tail cyclic analogues of LL37 and histatin 5

Kamysz

Sikorska

Karafova

et al. 2012

Journal of Peptide Science

View full text Add to dashboard Cite

LL37 and histatin 5 are antimicrobial peptides. LL37 exhibits killing activity against a broad spectrum of pathogens, whereas histatin 5 is primarily an antifungal agent. Head-to-tail cyclization of histatin 5 did not affect its antimicrobial and haemolytic activity. The cyclic LL37 exhibits identical antifungal and haemolytic activity as does LL37. Its antimicrobial activity varied in one dilution depending on the kind of bacteria. The structure of cyclic peptides was studied by circular dichroism spectroscopy. Both peptides undergo a conformational change leading to stabilisation of their α-helical structure in the presence of negatively charged sodium dodecyl sulfate micelles. However, with cyclic histatin 5, the presence of Zn(2+) ions is also necessary to fuse the peptide to the micelle. The specific action of the Zn(2+) ions is attributed to the presence of a zinc-binding motif, His-Glu-X-X-His. It has been speculated that this zinc complexing may be related to the well-established anticandidal activity. In the case of cyclic LL37, also the presence of a zwitterionic dodecylphosphocholine micelle induces formation of the helical structure. A microwave-assisted procedure for the cleavage of a peptide from the 2-chlorotrityl chloride resin was, for the first time, successfully used to obtain protected peptide fragments that can be applied to the preparation of head-to-tail cyclopeptides or to condensation of peptidic fragments.

show abstract

“…Since 1992, when Wang described the use of the kitchen microwave oven in SPPS1, a number of reports have been published that show advantages of microwave irradiation in organic chemistry, including peptide synthesis (loading of the resin2–6, coupling of amino acids7, 8 or in cleavage of peptides from solid support9).…”

Section: Introductionmentioning

confidence: 99%

Microwave‐assisted TFA cleavage of peptides from Merrifield resin

Kluczyk

Stefanowicz

Szewczuk

2009

Journal of Peptide Science

View full text Add to dashboard Cite

Microwave-assisted (MW) reactions are of special interest to the chemical community due to faster reaction times, cleaner reactions and higher product yields. The adaptation of MW to solid phase peptide synthesis resulted in spectacular syntheses of difficult peptides. In the case of Merrifield support, used frequently in synthesis of special peptides, the conditions used in product cleavage are not compatible with off-resin monitoring of the reaction progress. The application of MW irradiation in product removal from Merrifield resin using trifluoroacetic acid (TFA) was investigated using model tetrapeptides and the effects were compared with standard trifluoromethanesulphonic acid (TFMSA) cleavage using elemental analysis as well as chromatographic (HPLC) and spectroscopic (IR) methods. The deprotection of benzyloxycarbonyl and benzyl groups in synthetic bioactive peptides was analyzed using LC-MS and MS/MS experiments. In a 5 min microwave-assisted TFA reaction at low temperature, the majority of product is released from the resin, making the analytical scale MW-assisted procedure a method of choice in monitoring the reactions carried out on Merrifield resin due to the short reaction time and compatibility with HPLC and ESI-MS conditions.

show abstract

Solid-Phase Methods for the Microwave-Assisted Synthesis of Heterocycles

Cited by 14 publications

References 161 publications

Synthesis of bis-thiazolidin-4-ones from N,N,N″-(1,ω-alkanediyl)bis(N″-organylthiourea) derivatives

Synthesis of bis-thiazolidin-4-ones from N,N,N″-(1,ω-alkanediyl)bis(N″-organylthiourea) derivatives

Synthesis, biological activity and conformational analysis of head‐to‐tail cyclic analogues of LL37 and histatin 5

Microwave‐assisted TFA cleavage of peptides from Merrifield resin

Contact Info

Product

Resources

About