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Understanding Tetrahydropyranyl as a Protecting Group in Peptide Chemistry
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نویسنده
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sharma a. ,ramos-tomillero i. ,el-faham a. ,nicolas e. ,rodriguez h. ,de la torre b.g. ,albericio f.
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منبع
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chemistryopen - 2017 - دوره : 6 - شماره : 2 - صفحه:168 -177
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چکیده
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Tetrahydropyranyl (thp) is recognized as a useful protecting group for alcohols in organic synthesis. it has several advantages,including low cost,ease of introduction,general stability to most non-acidic reagents,it confers good solubility,and the ease with which it can be removed if the functional group it protects requires manipulation. however,little attention has been paid to thp in peptide chemistry. provided here is a concise analysis of the thp protection of various amino acid functionalities (oh,sh,nh and cooh) and its application to peptide synthesis. thp is a useful moiety for the side-chain protection of serine,threonine and cysteine and is suitable for the fmoc/tbu solid-phase peptide synthesis strategy. the immobilized version of 3,4-dihydro-2h-pyran,the so-called ellman resin,is also discussed as a useful solid support for anchoring the side chains of serine,threonine and tryptophan residues. © 2017 the authors. published by wiley-vch verlag gmbh & co. kgaa.
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کلیدواژه
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4-dihydro-2H-pyran; hydroxyl groups; protecting groups; tetrahydropyranyl group; thiols
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آدرس
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catalysis and peptide research unit,school of health sciences,university of kwazulu-natal,durban,4001, South Africa, inorganic and organic chemistry department,university of barcelona,martí franqués 1—11,barcelona,08028, Spain, department of chemistry,college of science,king saud university,p.o. box 2455,riyadh,11451,saudi arabia,department of chemistry,faculty of science,alexandria university,p.o. box 426,ibrahimia,alexandria,21321, Egypt, inorganic and organic chemistry department,university of barcelona,martí franqués 1—11,barcelona,08028, Spain, school of chemistry,yachay tech,yachay city of knowledge,urcuqui, Ecuador, catalysis and peptide research unit,school of health sciences,university of kwazulu-natal,durban,4001,south africa,school of laboratory of medicine & medical sciences,university of kwazulu-natal,durban,4001, South Africa, catalysis and peptide research unit,school of health sciences,university of kwazulu-natal,durban,4001,south africa,inorganic and organic chemistry department,university of barcelona,martí franqués 1—11,barcelona,08028,spain,department of chemistry,college of science,king saud university,p.o. box 2455,riyadh,11451,saudi arabia,school of chemistry & physics,university of kwazulu-natal,durban,4001,south africa,ciber-bbn,networking centre on bioengineering,biomaterials and nanomedicine,barcelona science park,baldiri reixac 10—12,barcelona,08028, Spain
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Authors
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