Next Article in Journal
Synthesis of a Novel Series of Phosphonate-Functionalized 1,2,3-Triazoles as Potential Candidates for Allosteric Modulation of α7 Nicotinic Acetylcholine Receptors
Previous Article in Journal
Electrochemical Reduction of Oxygen Using a Metal–Organic Complex of Cu2+
 
 
Search for Articles:
Title / Keyword
Author / Affiliation / Email
Journal
Article Type
 
 
Advanced Search
 
Section
Special Issue
Volume
Issue
Number
Page
 
Journals
Proceedings
Volume 9
Issue 1
10.3390/ecsoc-22-05769
proceedings-logo
Submit to this Journal
► Article Menu

Article Menu

share Share announcement Help format_quote Cite question_answer Discuss in SciProfiles thumb_up
...
Endorse textsms
...
Comment
first_page
settings
Order Article Reprints
Font Type:
Arial Georgia Verdana
Font Size:
Aa Aa Aa
Line Spacing:
Column Width:
Background:
Proceeding Paper

Efficient Synthesis of New α-β-Unsaturated Alkyl-Ester Peptide-Linked Chiral Amines †

by
Oscar Villanueva-Kasis
1,2,
Denisse A. de Loera
2,
Sandra L. Castañón-Alonso
1,
Armando Domínguez-Ortiz
1,
Leticia Lomas-Romero
1,
Ilich A. Ibarra
3,*,
Eduardo González-Zamora
1,* and
Alejandro Islas-Jácome
1,*
1
Departamento de Química, Universidad Autónoma Metropolitana-Iztapalapa, San Rafael Atlixco 186, Col. Vicentina, C.P. 09340 Iztapalapa, Ciudad de México, México
2
Facultad de Ciencias Químicas, Universidad Autónoma de San Luís Potosí, Av. Manuel Nava 6, Zona Universitaria, C.P. 78210 San Luis Potosí, S.L.P., México
3
Laboratorio de Fisicoquímica y Reactividad de Superficies, Instituto de Investigaciones en Materiales, Universidad Nacional Autónoma de México, Circuito Exterior S/N, Ciudad Universitaria, C.P. 04510 Coyoacán, Ciudad de México, México
*
Authors to whom correspondence should be addressed.
†
Presented at the 22nd International Electronic Conference on Synthetic Organic Chemistry, 15 November–15 December 2018; Available Online: https://sciforum.net/conference/ecsoc-22.
Proceedings 2019, 9(1), 34; https://doi.org/10.3390/ecsoc-22-05769
Published: 14 November 2018
(This article belongs to the Proceedings of 22nd International Electronic Conference on Synthetic Organic Chemistry)
Versions Notes

Abstract

Four new α-β-unsaturated alkyl-ester chiral amines were synthesized in excellent yields (77–95%) via peptide couplings from their corresponding α-β-unsaturated alkyl-ester anilines and N-Boc protected chiral aminoacids. To our delight, these polyfunctionalized compounds are being used as starting reagents in Ugi-type three-component reactions (Ugi-3CR) together with alkyl- and aryl-aldehydes and a chain-ring tautomerizable amino acid-containing isocyanide to synthesize novel oxazole-based macrocycle precursors. Thus, the aim of this communication is to show our most recent results of the synthesis and use of new and complex chiral amines to assemble macrocyclic polypeptides with potential application in medicinal chemistry, such as the post-surgical antibiotic Vancomycin.
Keywords: Chiral amines; α-β-unsaturated alkyl-ester anilines; peptide synthesis; N-Boc protection-deprotection; multicomponent reactions; Ugi-3CR; chemoselective reductions Chiral amines; α-β-unsaturated alkyl-ester anilines; peptide synthesis; N-Boc protection-deprotection; multicomponent reactions; Ugi-3CR; chemoselective reductions

Share and Cite

MDPI and ACS Style

Villanueva-Kasis, O.; Loera, D.A.d.; Castañón-Alonso, S.L.; Domínguez-Ortiz, A.; Lomas-Romero, L.; Ibarra, I.A.; González-Zamora, E.; Islas-Jácome, A. Efficient Synthesis of New α-β-Unsaturated Alkyl-Ester Peptide-Linked Chiral Amines. Proceedings 2019, 9, 34. https://doi.org/10.3390/ecsoc-22-05769

AMA Style

Villanueva-Kasis O, Loera DAd, Castañón-Alonso SL, Domínguez-Ortiz A, Lomas-Romero L, Ibarra IA, González-Zamora E, Islas-Jácome A. Efficient Synthesis of New α-β-Unsaturated Alkyl-Ester Peptide-Linked Chiral Amines. Proceedings. 2019; 9(1):34. https://doi.org/10.3390/ecsoc-22-05769

Chicago/Turabian Style

Villanueva-Kasis, Oscar, Denisse A. de Loera, Sandra L. Castañón-Alonso, Armando Domínguez-Ortiz, Leticia Lomas-Romero, Ilich A. Ibarra, Eduardo González-Zamora, and Alejandro Islas-Jácome. 2019. "Efficient Synthesis of New α-β-Unsaturated Alkyl-Ester Peptide-Linked Chiral Amines" Proceedings 9, no. 1: 34. https://doi.org/10.3390/ecsoc-22-05769

APA Style

Villanueva-Kasis, O., Loera, D. A. d., Castañón-Alonso, S. L., Domínguez-Ortiz, A., Lomas-Romero, L., Ibarra, I. A., González-Zamora, E., & Islas-Jácome, A. (2019). Efficient Synthesis of New α-β-Unsaturated Alkyl-Ester Peptide-Linked Chiral Amines. Proceedings, 9(1), 34. https://doi.org/10.3390/ecsoc-22-05769

Article Metrics

Back to TopTop