دورية أكاديمية
أعرض في EDS

One-pot organocatalytic/multicomponent approach for the preparation of novel enantioenriched non-natural selenium-based peptoids and peptide-peptoid conjugates.

التفاصيل البيبلوغرافية
العنوان: One-pot organocatalytic/multicomponent approach for the preparation of novel enantioenriched non-natural selenium-based peptoids and peptide-peptoid conjugates.
المؤلفون: de la Torre AF; Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad de Concepción, Edmundo Larenas 234-interior -Casilla 160-C, Concepción, Chile. afernandezd@udec.cl.; Center of Excellence for Research in Sustainable Chemistry (CERSusChem), Department of Chemistry, Federal University of São Carlos - UFSCar, Rodovia Washington Luís, km 235 - SP-310, São Carlos, São Paulo, 13565-905, Brazil. afernandezd@udec.cl., Ali A; Department of Chemistry, University of Sargodha, Sargodha, 40100, Pakistan., Galetto FZ; Departamento de Química, Universidade Federal de Santa Catarina, Florianópolis, SC, 88040-900, Brazil., Braga AL; Departamento de Química, Universidade Federal de Santa Catarina, Florianópolis, SC, 88040-900, Brazil. braga.antonio@ufsc.br., Delgado JAC; Center of Excellence for Research in Sustainable Chemistry (CERSusChem), Department of Chemistry, Federal University of São Carlos - UFSCar, Rodovia Washington Luís, km 235 - SP-310, São Carlos, São Paulo, 13565-905, Brazil., Paixão MW; Center of Excellence for Research in Sustainable Chemistry (CERSusChem), Department of Chemistry, Federal University of São Carlos - UFSCar, Rodovia Washington Luís, km 235 - SP-310, São Carlos, São Paulo, 13565-905, Brazil. marelloweber@gmail.com.
المصدر: Molecular diversity [Mol Divers] 2020 Feb; Vol. 24 (1), pp. 1-10. Date of Electronic Publication: 2019 Feb 18.
نوع المنشور: Journal Article
اللغة: English
بيانات الدورية: Publisher: ESCOM Science Publishers Country of Publication: Netherlands NLM ID: 9516534 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1573-501X (Electronic) Linking ISSN: 13811991 NLM ISO Abbreviation: Mol Divers Subsets: MEDLINE
أسماء مطبوعة: Original Publication: Leiden, The Netherlands : ESCOM Science Publishers, c1995-
مواضيع طبية MeSH: Chemistry Techniques, Synthetic* , Organic Chemistry Phenomena* , Selenium*, Peptoids/*chemical synthesis, Magnetic Resonance Spectroscopy
مستخلص: A combined organocatalytic and multicomponent synthetic approach was designed for the preparation of selenium-based peptoids and peptide-peptoid conjugates. This single-step synthetic protocol comprises the organocatalytic asymmetric insertion of phenylselenium in the aldehyde moiety followed by the Ugi four-component reaction which results in obtaining the desired compounds in good-to-moderate yields and with good-to-excellent levels of stereoselectivity.
References: Org Biomol Chem. 2012 Dec 21;10(47):9330-3. (PMID: 23114693)
Chem Biodivers. 2008 Mar;5(3):375-88. (PMID: 18357547)
Dalton Trans. 2011 Nov 21;40(43):11347-55. (PMID: 21904736)
J Pept Sci. 2008 Dec;14(12):1223-39. (PMID: 18951416)
J Am Chem Soc. 2012 Jan 11;134(1):138-41. (PMID: 22136421)
Chem Biol Drug Des. 2009 Sep;74(3):302-8. (PMID: 19703033)
Chem Rev. 2006 Jan;106(1):17-89. (PMID: 16402771)
Antioxid Redox Signal. 2010 Apr 1;12(7):881-92. (PMID: 19747061)
Org Biomol Chem. 2012 Aug 28;10(32):6595-9. (PMID: 22801447)
J Pept Sci. 1997 Nov-Dec;3(6):442-53. (PMID: 9467972)
J Org Chem. 2013 Oct 18;78(20):10221-32. (PMID: 24053491)
Org Chem Front. 2014 Sep 1;1(7):834-837. (PMID: 25147729)
J Am Chem Soc. 2005 Dec 28;127(51):18296-304. (PMID: 16366584)
Chem Commun (Camb). 2017 Mar 28;53(26):3777-3780. (PMID: 28304024)
Org Biomol Chem. 2012 Oct 14;10(38):7681-4. (PMID: 22918441)
Angew Chem Int Ed Engl. 2005 Jan 21;44(5):794-7. (PMID: 15657970)
Angew Chem Int Ed Engl. 2015 Jun 22;54(26):7621-5. (PMID: 25967546)
Angew Chem Int Ed Engl. 2005 Mar 4;44(11):1602-34. (PMID: 15719349)
Chem Soc Rev. 2012 Dec 7;41(23):7712-22. (PMID: 22918262)
Org Lett. 2001 May 3;3(9):1331-4. (PMID: 11348227)
Bioorg Med Chem. 2016 Nov 15;24(22):5762-5770. (PMID: 27681239)
J Phys Chem B. 2014 Jan 16;118(2):492-500. (PMID: 24354504)
Chem Commun (Camb). 2009 Aug 21;(31):4702-4. (PMID: 19641815)
Trends Biochem Sci. 1996 Jun;21(6):203-8. (PMID: 8744353)
Chem Soc Rev. 2012 May 21;41(10):3969-4009. (PMID: 22546840)
Org Biomol Chem. 2009 Nov 21;7(22):4753-62. (PMID: 19865713)
J Org Chem. 2016 Feb 5;81(3):803-9. (PMID: 26720907)
Med Res Rev. 2000 Jul;20(4):304-22. (PMID: 10861729)
Biol Chem. 2007 Oct;388(10):997-1006. (PMID: 17937613)
Chem Commun (Camb). 2006 Feb 7;(5):541-3. (PMID: 16432576)
Science. 2003 May 30;300(5624):1439-43. (PMID: 12775843)
Nature. 2000 Sep 28;407(6803):463, 465. (PMID: 11028985)
Angew Chem Int Ed Engl. 2003 Oct 13;42(39):4742-58. (PMID: 14562341)
Chem Rev. 2001 Jul;101(7):2125-79. (PMID: 11710243)
Adv Nutr. 2011 Mar;2(2):122-8. (PMID: 22332041)
ACS Chem Biol. 2016 Apr 15;11(4):821-41. (PMID: 26949981)
Physiol Rev. 2014 Jul;94(3):739-77. (PMID: 24987004)
J Med Chem. 1996 May 10;39(10):2040-6. (PMID: 8642562)
Mol Microbiol. 1991 Mar;5(3):515-20. (PMID: 1828528)
J Pept Sci. 2008 May;14(5):637-47. (PMID: 18035847)
Angew Chem Int Ed Engl. 2007;46(36):6882-5. (PMID: 17680576)
Org Lett. 2000 Nov 16;2(23):3603-6. (PMID: 11073655)
معلومات مُعتمدة: CNPq (14/403846) CNPq; 3170003 Fondecyt
فهرسة مساهمة: Keywords: Multicomponent reactions; Organocatalysis; Peptoids; Selenocysteine; Ugi reaction
المشرفين على المادة: 0 (Peptoids)
H6241UJ22B (Selenium)
تواريخ الأحداث: Date Created: 20190220 Date Completed: 20201013 Latest Revision: 20201013
رمز التحديث: 20240628
DOI: 10.1007/s11030-019-09923-w
PMID: 30778816
قاعدة البيانات: MEDLINE
الوصف
تدمد:1573-501X
DOI:10.1007/s11030-019-09923-w