An efficient protocol for the solid-phase synthesis of glycopeptides under microwave irradiation

García-Martín, Fayna; Hinou, Hiroshi; Matsushita, Takahiko; Hayakawa, Shun; Nishimura, Shin‐Ichiro

doi:10.1039/c2ob06532k

Cited by 22 publications

(29 citation statements)

References 32 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Apart from their effects on cell membranes, microwaves cause non-thermal acceleration of enzymatic reactions in microbial cells, such as non-aqueous esterification (formation of ester-type of chemical compounds without participation of water), and this effect is substrate concentration-dependent [28]. Moreover, microwaves can accelerate synthesis of glycopeptides in vitro (out of the living cells), which may occur in microbial cells, changing their functions [29]. It was shown in human cells that microwaves could decrease the expression and activity of certain functional proteins that cause apoptosis.…”

Section: Possible Mechanisms Of Non-thermal Effects Of Microwaves On mentioning

confidence: 99%

The effects of microwave radiation on microbial cultures

Janković¹,

Milosev²,

Novaković³

2014

Hosp Pharm Int Multi J

View full text Add to dashboard Cite

Microwaves are non-ionizing electromagnetic waves with frequencies between 0.3 and 300 GHz. Both humans and microorganisms living on the human body are exposed to significant doses of microwave radiation in everyday life. Whether and how microwave radiation could influence the viability and growth of microorganisms is the subject of this educational paper. Studies on the effects of microwaves on the growth of microbial cultures were searched for in biomedical journals indexed in MEDLINE from 1966 to 2012. The published studies showed that microwaves produce significant effects on the growth of microbial cultures, which vary from the killing of microorganisms to enhancement of their growth. The nature and extent of the effect depend on the frequency of microwaves and the total energy absorbed by the microorganisms. Low energy, low frequency microwaves enhance the growth of microorganisms, whereas high energy, high frequency microwaves destroy the microorganisms. However, neither the effects of a wide spectrum of frequencies nor the effects of a wide range of absorbed energies have been investigated. Considering the potentially deleterious influence of microwaves on the symbiotic balance between microorganisms and the human host, further research on the effects of the complete frequency and energy spectra of microwave radiation on the growth of microorganisms is necessary.

show abstract

Section: Possible Mechanisms Of Non-thermal Effects Of Microwaves On mentioning

confidence: 99%

The effects of microwave radiation on microbial cultures

Janković¹,

Milosev²,

Novaković³

2014

Hosp Pharm Int Multi J

View full text Add to dashboard Cite

show abstract

“…Briefly, this novel protocol involves incorporating glycosylated amino acids using only 1.2 equiv under microwave irradiation, after half of the coupling time, 1.2 equiv more coupling reagent is added to reactivate the free carboxylic acid. Thus, after 20 min of coupling time under microwave energy, the hindered and valuable glycan amino acids could be incorporated in high yield 38. Afterwards, the code tag is synthesized in the inner layer.…”

Section: Resultsmentioning

confidence: 99%

“…The coupling of non‐glycosylated amino acids (4 equiv) was carried out with HBTU–HOBt–DIEA (4:4:6) in DMF for 10 min assisted by MW energy. Glycosyl amino acids were achieved following double activation protocol 38. This method incorporates amino acids bearing carbohydrates by employing 1.2 equiv of glycosylated amino acids and the reagents PyBOP–HOAt–DIEA (1.2:1.2:1.8) in DMF.…”

Section: Methodsmentioning

confidence: 99%

Fast Epitope Mapping for the Anti‐MUC1 Monoclonal Antibody by Combining a One‐Bead‐One‐Glycopeptide Library and a Microarray Platform

García-Martín

Matsushita

Hinou

et al. 2014

Chemistry A European J

Self Cite

View full text Add to dashboard Cite

Anti-MUC1 monoclonal antibodies (mAbs) are powerful tools that can be used to recognize cancer-related MUC1 molecules, the O-glycosylation status of which is believed to affect binding affinity. We demonstrate the feasibility of using a rapid screening methodology to elucidate those effects. The approach involves i) "one-bead-one-compound"-based preparation of bilayer resins carrying glycopeptides on the shell and mass-tag tripeptides coding O-glycan patterns in the core, ii) on-resin screening with an anti-MUC1 mAb, iii) separating positive resins by utilizing secondary antibody conjugation with magnetic beads, and (iv) decoding the mass-tag that is detached from the positive resins pool by using mass spectrometric analysis. We tested a small library consisting of 27 MUC1 glycopeptides with different O-glycosylations against anti-MUC1 mAb clone VU-3C6. Qualitative mass-tag analysis showed that increasing the number of glycans leads to an increase in the binding affinity. Six glycopeptides selected from the library were validated by using a microarray-based assay. Our screening provides valuable information on O-glycosylations of epitopes leading to high affinity with mAb.

show abstract

“…Coupling reactions were conducted for 10 min. For the glycosyl amino acid coupling, a double activation protocol was carried out, employing N α ‐Fmoc‐glycosyl‐Ser/Thr amino acid (1.2 equiv) in combination with PyBOP (1.2 equiv), HOAt (1.2 equiv) and DIEA (2.5 equiv) in DMF. After 10 min under MW irradiation to maintain 50 °C, without filtering, 1.2 equiv of PyBOP‐HOAt were added and allowed to react for another 10 min.…”

Section: Discussionmentioning

confidence: 99%

Synthetic Mucin‐Like Glycopeptides as Versatile Tools to Measure Effects of Glycan Structure/Density/Position on the Interaction with Adhesion/Growth‐Regulatory Galectins in Arrays

Artigas

Hinou

García-Martín

et al. 2016

Chemistry An Asian Journal

Self Cite

View full text Add to dashboard Cite

Functional pairing of cellular glycoconjugates with tissue lectins is a highly selective process, whose determinative factors have not yet been fully delineated. Glycan structure and modes of presentation, that is, its position and density, can contribute to binding, as different members of a lectin family can regulate degrees of responsiveness to these factors. Using a peptide repeat sequence motif of the glycoprotein mucin-1, the principle of introducing synthetic (glyco)peptides with distinct variations in these three parameters to an array-based screening of tissue lectins is illustrated. Interaction profiles of seven adhesion/growth-regulatory galectins cover the range from intense signals with core 2 pentasaccharides and core 1 binding for galectins-3 and -5 to a lack of binding for galectin-1 and also the galectin-related protein, which was included as a negative control. Remarkably, the two tandem-repeat-type galectins-4 and -8 were distinguished by core 1 sialylation, as the two separated domains were. These results encourage further synthetic elaboration of the glycopeptide library and testing of the network of natural galectins and rationally engineered variants of the lectins.

show abstract

An efficient protocol for the solid-phase synthesis of glycopeptides under microwave irradiation

Cited by 22 publications

References 32 publications

The effects of microwave radiation on microbial cultures

The effects of microwave radiation on microbial cultures

Fast Epitope Mapping for the Anti‐MUC1 Monoclonal Antibody by Combining a One‐Bead‐One‐Glycopeptide Library and a Microarray Platform

Synthetic Mucin‐Like Glycopeptides as Versatile Tools to Measure Effects of Glycan Structure/Density/Position on the Interaction with Adhesion/Growth‐Regulatory Galectins in Arrays

Contact Info

Product

Resources

About