Oxyma及其衍生的新型偶联试剂
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摘要
偶联反应常使用碳二亚胺类化合物做偶联缩合剂,为了提高产率和抑制消旋化,会和偶联添加剂1-羟基苯并三氮唑类化合物联合使用。但是由于1-羟基苯并三氮唑类化合物性质不稳定,易燃易爆,有时副产物毒性大,故在使用上受到较大限制。近年来,人们发现Oxyma及其衍生物同样具有较好的催化活性,而且性质稳定,副产物易处理,毒性小,有些可以回收重复使用。我们对Oxyma及其衍生物的催化机理、结构特点、使用情况进行了介绍,认为Oxyma及其衍生物是一类绿色环保型偶联试剂,具有非常好的应用前景。
引文
[1]HELENA L,FREDRIK T,NICKLAS S,et al. Catalytic amide formation from non-activated carboxylic acids and amines[J]. Chemical Society Reviews,2014,45(24):2714
[2]YAMANO N,KAWASAKI N,IDA S,et al. Biodegradation of polyamide 4 in vivo[J]. Polymer Degradation&Stability,2017,137(5):281
[3]KUMAR A,ESPINOSA-JALAPA N A,LEITUS G,et al.Direct synthesis of amides by dehydrogenative coupling of amines with either alcohols or esters:manganese pincer complex as catalyst[J]. Angewandte Chemie,2017,129(20):15188
[4]CHEUNG C W,PLOEGER M L,HU X. Direct amidation of esters with nitroarenes[J]. Nature Communications,2017,8(2):14878
[5]KHATTAB S N. Cyanoacetamide-based oxime carbonates:an efficient,simple alternative for the introduction of Fmoc with minimal dipeptide formation[J]. Tetrahedron,2012,68(14):3056
[6]VALEUR E,BRADLEY M. Amide bond formation:beyond the myth of coupling reagents[J]. Chemical Society Reviews,2009,38(2):606
[7]SUBIROS-FUNOSAS R,KHATTAB S N,NIETO-RODRIGUEZ L,et al. Advances in acylation methodologies enabled by oxyma-based reagents[J]. Aldrichimica Acta,2015,46(1):21
[8]SUBIR S-FUNOSAS R,EL-FAHAM A,ALBERICIO F.Low-epimerization peptide bond formation with Oxyma pure:preparation of Z-L-Phg-Val-OMe[J]. Organic Syntheses,2003,90(5):306
[9]ELFAHAM A,AL M Z,ABDELMEGEED A,et al. Oxyma Pure/DIC:an efficient reagent for the synthesis of a novel series of 4-[2-(2-acetylaminophenyl)-2-oxo-acetylamino]benzoyl amino acid ester derivatives[J]. Molecules,2013,18(12):14747
[10]WANG Q,WANG Y,KUROSU M J O L. A new oxyma derivative for nonracemizable amide-forming reactions in water[J]. Organic Letters,2012,14(13):3372
[11]MITACHI K,KUROSU Y E,HAZLETT B T,et al. Oxyma-based phosphates for racemization-free peptide segment couplings[J]. Journal of Peptide Science,2016,22(3):186
[12]CHERKUPALLY P,ACOSTA G A,NIETO-RODRIGUEZ L,et al. K-Oxyma:a strong acylation-promoting,2-CTC resin-friendly coupling additive[J]. European Journal of Organic Chemistry,2013,2013(28):6372
[13]JAD Y E,KHATTAB S N,BG D L T,et al. Oxyma-B,an excellent racemization suppressor for peptide synthesis[J]. Organic and Biomolecular Chemistry,2014,12(42):8379
[14]JAD Y E,TORRE B G D L,GOVENDER T,et al. Oxyma-T,expanding the arsenal of coupling reagents[J].Tetrahedron Letters,2016,57(31):3523
[15]THALLURI K,NADIMPALLY K C,CHAKRAVARTY M P,et al. Ethyl 2-(tert-Butoxycarbonyloxyimino)-2-cyanoacetate(Boc-Oxyma)as coupling reagent for racemization-free esterification,thioesterification,amidation and peptide synthesis[J]. Advanced Synthesis and Catalysis,2013,355(2-3):448
[16]KHATTAB S N,SUBIR S-FUNOSAS R,EL-FAHAM A,et al. Oxime carbonates:novel reagents for the introduction of fmoc and alloc protecting groups,free of side reactions[J]. European Journal of Organic Chemistry,2010,2010(17):3275
[17]MANNE S R,THALLURI K,GIRI R S,et al. Ethyl 2-(tert-Butoxycarbonyloxyimino)-2-cyanoacetate(BocOxyma):an efficient reagent for the racemization free synthesis of ureas,carbamates and thiocarbamates via lossen rearrangement[J]. Advanced Synthesis&Catalysis,2017,359(1):168
[18]EL-FAHAM A,ALBERICIO F. COMU:A third generation of uronium-type coupling reagents[J]. Journal of Peptide Science,2010,16(1):6
[19]EL-FAHAM A,SUBIR3S F R,PROHENS R,et al. COMU:a safer and more effective replacement for benzotriazole-based uronium coupling reagents[J]. Chemistry,2010,15(37):9404
[20]KUMAR A,JAD Y E,DE L T,BEATRIZ G,et al. Re-evaluating the stability of COMU in different solvents[J].Journal of Peptide Science,2017,23(10):763
[21]GABRIEL C M,KEENER M,GALLOU F,et al. Amide and peptide bond formation in water at room temperature[J]. Org Lett,2016,47(2):3968
[22]SUBIR3S-FUNOSAS R,EL-FAHAM A,ALBERICIO F J O,et al. Py Ox P and Py Ox B:the Oxyma-based novel family of phosphonium salts[J]. Organic and Biomolecular Chemistry,2010,8(16):3665
[23]JAD Y E,KHATTAB S N,BG D L T,et al. TOMBU and COMBU as novel uronium-type peptide coupling reagents derived from Oxyma-B[J]. Molecules,2014,19(11):18953
[24]BRIEHL H,LUKOSCH A,WENTRUP C. Reactive nitrogenous molecules from Meldrum's acid derivatives,pyrrole-2,3-diones,and isoxazolones[J]. The Journal of Organic Chemistry,1984,49(15):2772
[25]EL-FAHAM A,SUBIR S-FUNOSAS R,ALBERICIO F J. A novel family of onium salts based upon isonitroso meldrum's acid proves useful as peptide coupling reagents[J]. European Journal of Organic Chemistry,2010,2010(19):3641
[2]YAMANO N,KAWASAKI N,IDA S,et al. Biodegradation of polyamide 4 in vivo[J]. Polymer Degradation&Stability,2017,137(5):281
[3]KUMAR A,ESPINOSA-JALAPA N A,LEITUS G,et al.Direct synthesis of amides by dehydrogenative coupling of amines with either alcohols or esters:manganese pincer complex as catalyst[J]. Angewandte Chemie,2017,129(20):15188
[4]CHEUNG C W,PLOEGER M L,HU X. Direct amidation of esters with nitroarenes[J]. Nature Communications,2017,8(2):14878
[5]KHATTAB S N. Cyanoacetamide-based oxime carbonates:an efficient,simple alternative for the introduction of Fmoc with minimal dipeptide formation[J]. Tetrahedron,2012,68(14):3056
[6]VALEUR E,BRADLEY M. Amide bond formation:beyond the myth of coupling reagents[J]. Chemical Society Reviews,2009,38(2):606
[7]SUBIROS-FUNOSAS R,KHATTAB S N,NIETO-RODRIGUEZ L,et al. Advances in acylation methodologies enabled by oxyma-based reagents[J]. Aldrichimica Acta,2015,46(1):21
[8]SUBIR S-FUNOSAS R,EL-FAHAM A,ALBERICIO F.Low-epimerization peptide bond formation with Oxyma pure:preparation of Z-L-Phg-Val-OMe[J]. Organic Syntheses,2003,90(5):306
[9]ELFAHAM A,AL M Z,ABDELMEGEED A,et al. Oxyma Pure/DIC:an efficient reagent for the synthesis of a novel series of 4-[2-(2-acetylaminophenyl)-2-oxo-acetylamino]benzoyl amino acid ester derivatives[J]. Molecules,2013,18(12):14747
[10]WANG Q,WANG Y,KUROSU M J O L. A new oxyma derivative for nonracemizable amide-forming reactions in water[J]. Organic Letters,2012,14(13):3372
[11]MITACHI K,KUROSU Y E,HAZLETT B T,et al. Oxyma-based phosphates for racemization-free peptide segment couplings[J]. Journal of Peptide Science,2016,22(3):186
[12]CHERKUPALLY P,ACOSTA G A,NIETO-RODRIGUEZ L,et al. K-Oxyma:a strong acylation-promoting,2-CTC resin-friendly coupling additive[J]. European Journal of Organic Chemistry,2013,2013(28):6372
[13]JAD Y E,KHATTAB S N,BG D L T,et al. Oxyma-B,an excellent racemization suppressor for peptide synthesis[J]. Organic and Biomolecular Chemistry,2014,12(42):8379
[14]JAD Y E,TORRE B G D L,GOVENDER T,et al. Oxyma-T,expanding the arsenal of coupling reagents[J].Tetrahedron Letters,2016,57(31):3523
[15]THALLURI K,NADIMPALLY K C,CHAKRAVARTY M P,et al. Ethyl 2-(tert-Butoxycarbonyloxyimino)-2-cyanoacetate(Boc-Oxyma)as coupling reagent for racemization-free esterification,thioesterification,amidation and peptide synthesis[J]. Advanced Synthesis and Catalysis,2013,355(2-3):448
[16]KHATTAB S N,SUBIR S-FUNOSAS R,EL-FAHAM A,et al. Oxime carbonates:novel reagents for the introduction of fmoc and alloc protecting groups,free of side reactions[J]. European Journal of Organic Chemistry,2010,2010(17):3275
[17]MANNE S R,THALLURI K,GIRI R S,et al. Ethyl 2-(tert-Butoxycarbonyloxyimino)-2-cyanoacetate(BocOxyma):an efficient reagent for the racemization free synthesis of ureas,carbamates and thiocarbamates via lossen rearrangement[J]. Advanced Synthesis&Catalysis,2017,359(1):168
[18]EL-FAHAM A,ALBERICIO F. COMU:A third generation of uronium-type coupling reagents[J]. Journal of Peptide Science,2010,16(1):6
[19]EL-FAHAM A,SUBIR3S F R,PROHENS R,et al. COMU:a safer and more effective replacement for benzotriazole-based uronium coupling reagents[J]. Chemistry,2010,15(37):9404
[20]KUMAR A,JAD Y E,DE L T,BEATRIZ G,et al. Re-evaluating the stability of COMU in different solvents[J].Journal of Peptide Science,2017,23(10):763
[21]GABRIEL C M,KEENER M,GALLOU F,et al. Amide and peptide bond formation in water at room temperature[J]. Org Lett,2016,47(2):3968
[22]SUBIR3S-FUNOSAS R,EL-FAHAM A,ALBERICIO F J O,et al. Py Ox P and Py Ox B:the Oxyma-based novel family of phosphonium salts[J]. Organic and Biomolecular Chemistry,2010,8(16):3665
[23]JAD Y E,KHATTAB S N,BG D L T,et al. TOMBU and COMBU as novel uronium-type peptide coupling reagents derived from Oxyma-B[J]. Molecules,2014,19(11):18953
[24]BRIEHL H,LUKOSCH A,WENTRUP C. Reactive nitrogenous molecules from Meldrum's acid derivatives,pyrrole-2,3-diones,and isoxazolones[J]. The Journal of Organic Chemistry,1984,49(15):2772
[25]EL-FAHAM A,SUBIR S-FUNOSAS R,ALBERICIO F J. A novel family of onium salts based upon isonitroso meldrum's acid proves useful as peptide coupling reagents[J]. European Journal of Organic Chemistry,2010,2010(19):3641