Semipermanent C-Terminal Carboxylic Acid Protecting Group: Application to Solubilizing Peptides and Fragment Condensation

2014 ◽  
Vol 17 (2) ◽  
pp. 294-297 ◽  
Author(s):  
Marta Paradís-Bas ◽  
Judit Tulla-Puche ◽  
Fernando Albericio
Keyword(s):  
Carboxylic Acid ◽  
Protecting Group ◽  
Fragment Condensation

Synthesis of the major encephalitogenic determinant of myelin basic protein and the 13C N.M.R. of some protected intermediates

1977 ◽  
Vol 30 (11) ◽  
pp. 2533 ◽  
Author(s):  
SJ Pasaribu
Keyword(s):  
Myelin Basic Protein ◽  
Catalytic Hydrogenation ◽  
Basic Protein ◽  
Side Chain ◽  
Benzyl Ether ◽  
Protecting Group ◽  
Fragment Condensation

The main encephalitogenic determinant of bovine myelin basic protein (MBP 114-122) has been synthesized through fragment condensation of tetrapeptide, Boc-Phe-Ser-Trp-Gly-OH, and penta-peptide, H-Ala- Glu(OBzl)-Gly-Gln-Lys(Nε-Cbz)-Obzl. It was observed that the benzyl ether protecting group of the serine side chain was not removed during catalytic hydrogenation (Pd/C-H2) of the tetrapeptide, Boc-Phe- Ser(OBzl)-Trp-Gly-OBzl. 13C N.M.R. spectra of some other intermediates are discussed.

Flavonoid intermediates for the synthesis of mopanol trimethyl ether[trans-trans-7,7',8'-Trimethoxyisochromano(4',3':2,3)chroman-4-ol]

1976 ◽  
Vol 29 (1) ◽  
pp. 191 ◽  
Author(s):  
JW Clark-Lewis ◽  
DP Cox
Keyword(s):  
Carboxylic Acid ◽  
Potassium Carbonate ◽  
Dimethyl Sulphate ◽  
Metal Hydrides ◽  
Cyclic Ether ◽  
Protecting Group ◽  
Model Compounds ◽  
Initial Product ◽  
Dibenzyl Ether ◽  
Trimethyl Ether

Preparation of a number of intermediates for the synthesis of (�)-mopanol trimethyl ether is described, together with exploratory reactions with model compounds, and especially with 7-methoxyflavanone-2'-carboxylic acid. 7-Methoxyflavan-4-ol, the initial product from reduction of 7-methoxyflavanone-2'-carboxylic acid with complex metal hydrides, was found to undergo facile dehydration to a novel intramolecular dibenzyl ether [the cyclic ether (19)*]. It was noted that the methoxymethyl group, which may be used as a protecting group for phenols, did not survive the conditions of methylation with dimethyl sulphate and potassium carbonate in acetone.

Synthesis and properties of oxytocin analogues modified in the tripeptide side chain

1984 ◽  
Vol 49 (3) ◽  
pp. 642-652 ◽  
Author(s):  
Zdenko Procházka ◽  
Michal Lebl ◽  
Tomislav Barth ◽  
Jan Hlaváček ◽  
Antonín Trka ◽  
...  
Keyword(s):  
Nmr Spectroscopy ◽  
Carboxylic Acid ◽  
Biological Activities ◽  
The Other ◽  
Side Chain ◽  
H Nmr ◽  
Fragment Condensation

Two oxytocin analogues were synthesized by fragment condensation (6 + 3) in the presence of dicyclohexylcarbodiimide and 1-hydroxybenzotriazole. In one of the analogues, proline in the position 7 and leucine in the position 8 were substituted by 2-[1-(2-oxo-3-aminopyrrolidinyl)]-4-methylpentanoic acid, in the other proline was replaced by 1-aminocyclopropane-1-carboxylic acid. Biological activities of the first analogue were strongly reduced and dissociation of the uterotonic and galoctogogic activities was observed with both the analogues. The structure of 2-(3-tert-butyloxycarbonylaminopyrrolidin-2-on-1-yl)-4-methylpentanoylglycine and its amide was confirmed by mass and 1 H NMR spectroscopy.

scholarly journals Exploring hydrogen peroxide responsive thiazolidinone-based prodrugs

2015 ◽  
Vol 51 (33) ◽  
pp. 7116-7119 ◽  
Author(s):  
Christian Perez ◽  
Jean-Philippe Monserrat ◽  
Yao Chen ◽  
Seth M. Cohen
Keyword(s):  
Hydrogen Peroxide ◽  
Carboxylic Acid ◽  
Protecting Group

A thiazolidinone moiety was found to serve as a protecting group for releasing carboxylic acid-containing therapeutics in the presence of hydrogen peroxide.

scholarly journals Evaluation of a 7-Methoxycoumarin-3-carboxylic Acid Ester Derivative as a Fluorescent, Cell-Cleavable, Phosphonate Protecting Group

ChemBioChem ◽  
2015 ◽  
Vol 17 (1) ◽  
pp. 52-55 ◽  
Author(s):  
Andrew J. Wiemer ◽  
Rebekah R. Shippy ◽  
Ashley M. Kilcollins ◽  
Jin Li ◽  
Chia-Hung Christine Hsiao ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Acid Ester ◽  
Protecting Group ◽  
Fluorescent Cell ◽  
Carboxylic Acid Ester ◽  
Ester Derivative

Procedure-Economical, Enantioselective Total Syntheses of Polycyclic Natural Products and Analogues Containing a 3a-Hydroxyhexahydropyrrolo[2,3-b]indole-2-carboxylic Acid Residue

Synlett ◽  
2020 ◽  
Vol 31 (17) ◽  
pp. 1681-1690
Author(s):  
Pei-Qiang Huang
Keyword(s):  
Natural Products ◽  
Carboxylic Acid ◽  
Tandem Reactions ◽  
Protecting Group ◽  
Future Perspectives ◽  
Total Syntheses ◽  
Bioactive Natural Products ◽  
Regioselective Reactions ◽  
Enantioselective Syntheses

The 3a-hydroxyhexahydropyrrolo[2,3-b]indole-2-carboxylic acid (HPIC) residue and its aza-analogue are found in many bioactive natural products. In this account, short divergent total syntheses of several such natural products, diastereomers and analogues are described. It is demonstrated that by appropriate combination of different efficient tactics such as biomimetic/bio-inspired synthesis, chemo/regioselective reactions, umpolung of regioselectivity and/or reactivity, and tandem reactions, the enantioselective syntheses of polycyclic molecules such as (+)-asperlicin E and (–)-robustanoids A and B can be achieved in a protecting-group-free and redox-economical manner, in only three to four steps starting from l-tryptophan.1 Introduction2 Strategic Considerations2.1 Occurrence of HO-HPIC and HO-aza-HPIC Residues in Natural Products2.2 Biosyntheses of HO-HPIC and HO-aza-HPIC Residues2.3 Chemical Syntheses of HO-HPIC and HO-aza-HPIC Residues3 Procedure-Economical Syntheses of HO-HPIC-Containing Natural Products3.1 Protecting-Group-Free Syntheses of Asperlicin E, Its Diastereomer, and an Analogue3.2 Divergent Syntheses of (–)-Robustanoids A and B, a Diastereomer, and Analogues4 Conclusion and Future Perspectives

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