Solid-phase synthesis of peptide selenoesters via a side-chain anchoring strategy

CuO nanostructures were successfully synthesized using NaOH and Cu(NO3)2 as starting materials by an aminated lignin (AL)-assisted solid-phase method.

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Solid-phase synthesis of N-(buta-2,3-dien-1-yl)amides by the Crabbé reaction

Canadian Journal of Chemistry ◽

10.1139/cjc-2012-0255 ◽

2013 ◽

Vol 91 (1) ◽

pp. 38-42

Author(s):

Tuomo Leikoski ◽

Pauli Wrigstedt ◽

Jorma Matikainen ◽

Jussi Sipilä ◽

Jari Yli-Kauhaluoma

Keyword(s):

Trifluoroacetic Acid ◽

Solid Phase Synthesis ◽

Solid Phase ◽

Phase Method ◽

Protecting Group ◽

Product Diversity ◽

Phase Synthesis ◽

Solid Phase Method ◽

Merrifield Resin ◽

Polymer Supported

The Crabbé homologation of polymer-supported propargylamine with paraformaldehyde, CuI, and dicyclohexylamine in 1,4-dioxane at 100 °C, followed by cleavage with dilute trifluoroacetic acid, furnishes N-(buta-2,3-dien-1-yl)amides as isolable products. The N-acyltriazene linker on Merrifield resin serves simultaneously as a protecting group for the nucleophilic primary amine. The product diversity is achieved by altering the acyl chloride in the acylation of the triazene linker. In addition to being a new route to nitrogen-containing allenes, our solid-phase method enables immobilization of these reactive cumulated dienes for further synthetic operations.

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Comparison of the Potency of 8-L-Arginine, 8-D-Arginine and 8-D-Homoarginine Vasopressin Analogs with Substituted Phenylalanine in Position 2

Collection of Czechoslovak Chemical Communications ◽

10.1135/cccc19941439 ◽

1994 ◽

Vol 59 (6) ◽

pp. 1439-1450 ◽

Cited By ~ 2

Author(s):

Miroslava Žertová ◽

Jiřina Slaninová ◽

Zdenko Procházka

Keyword(s):

Amino Acid ◽

Solid Phase Synthesis ◽

Solid Phase ◽

Basic Amino Acid ◽

The Other ◽

Side Chain ◽

Inhibitory Potency ◽

Phase Synthesis ◽

Other Hand ◽

Order Of Magnitude

An analysis of the uterotonic potencies of all analogs having substituted L- or D-tyrosine or -phenylalanine in position 2 and L-arginine, D-arginine or D-homoarginine in position 8 was made. The series of analogs already published was completed by the solid phase synthesis of ten new analogs having L- or D-Phe, L- or D-Phe(2-Et), L- or D-Phe(2,4,6-triMe) or D-Tyr(Me) in position 2 and either L- or D-arginine in position 8. All newly synthesized analogs were found to be uterotonic inhibitors. Deamination increases both the agonistic and antagonistic potency. In the case of phenylalanine analogs the change of configuration from L to D in position 2 enhances the uterotonic inhibition for more than 1 order of magnitude. The L to D change in position 8 enhances the inhibitory potency negligibly. Prolongation of the side chain of the D-basic amino acid in position 8 seems to decrease slightly the inhibitory potency if there is L-substituted amino acid in position 2. On the other hand there is a tendency to the increase of the inhibitory potency if there is D-substituted amino acid in position 2.

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