Variation in the activities of late stage filaggrin processing enzymes, calpain-1 and bleomycin hydrolase, together with pyrrolidone carboxylic acid levels, corneocyte phenotypes and plasmin activities in non-sun-exposed and sun-exposed facial stratum cor

2016 ◽  
Vol 38 (6) ◽  
pp. 567-575 ◽  
Author(s):  
N. Raj ◽  
R. Voegeli ◽  
A. V. Rawlings ◽  
B. Summers ◽  
M. R. Munday ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Late Stage ◽  
Processing Enzymes ◽  
Bleomycin Hydrolase ◽  
Pyrrolidone Carboxylic Acid

Pyrrolidone carboxylic acid (pyroglutamic acid) in normal plasma

1973 ◽  
Vol 29 (3) ◽  
pp. 346-347 ◽  
Author(s):  
M. G. Wolfersberger ◽  
J. Tabachnik
Keyword(s):  
Carboxylic Acid ◽  
Pyroglutamic Acid ◽  
Normal Plasma ◽  
Pyrrolidone Carboxylic Acid

scholarly journals Late-Stage β-C(sp3)–H Deuteration of Carboxylic Acids

2021 ◽  
Author(s):  
Alexander Uttry ◽  
Sourjya Mal ◽  
Manuel van Gemmeren
Keyword(s):  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
Late Stage ◽  
Bioactive Molecules ◽  
Wide Range ◽  
Catalyst Systems ◽  
First Time

Carboxylic acid moieties are highly abundant in bioactive molecules. In this study we describe the late-stage β-C(sp<sup>3</sup>)–H deuteration of free carboxylic acids. Based on our finding that the C–H activation with our catalyst systems is reversible, the de-deuteration process was first optimized. The resulting conditions involve ethylenediamine-based ligands, which, amongst other positions, for the first time enables the functionalization of non-activated methylene β-C(sp<sup>3</sup>)–H bonds and can be used to achieve the desired deuteration when using a deuterated solvent. The reported method allows for the functionalization of a wide range of free carboxylic acids with diverse substitution patterns, as well as the late-stage deuteration of bioactive molecules and related frameworks.

scholarly journals General α-Amino 1,3,4-Oxadiazole Synthesis via Late-Stage Reductive Functionalization of Tertiary Amides and Lactams

2021 ◽  
Author(s):  
Daniel Matheau-Raven ◽  
Darren J. Dixon
Keyword(s):  
Carboxylic Acid ◽  
Late Stage ◽  
Coupling Reaction ◽  
Reductive Activation ◽  
Mild Conditions ◽  
Drug Molecules ◽  
Drug Conjugates ◽  
Iminium Ion ◽  
Tertiary Amides ◽  
Coupling Partner

An iridium-catalyzed reductive three-component coupling reaction for the synthesis of medicinally relevant α-amino 1,3,4-oxadiazoles from abundant tertiary amides or lactams, carboxylic acids, and (N-isocyanimino) triphenylphosphorane, is described. Proceeding under mild conditions using (<1 mol%) Vaska’s complex (IrCl(CO)(PPh<sub>3</sub>)<sub>2</sub>) and tetramethyldisiloxane to access the key reactive iminium ion intermediates, a broad range of structurally complex α-amino 1,3,4-oxadiazole architectures were efficiently accessed from diverse carboxylic acid feedstock coupling partners. Extension to α-amino heterodiazole synthesis was readily achieved by exchanging the carboxylic acid coupling partner for C-, S-, or N-centered Brønsted acids, and provided rapid and modular access to these desirable, yet difficult-to-access, heterocycles. Furthermore, the high chemoselectivity of the catalytic reductive activation step allowed the late-stage functionalization of 10 drug molecules, including the synthesis of novel heterodiazole-fused drug-drug conjugates.<br>

Enzymic Formation of Pyrrolidone Carboxylic Acid from γ-Glutamyl Peptides

Nature ◽  
1956 ◽  
Vol 177 (4504) ◽  
pp. 377-378 ◽  
Author(s):  
GEORGE E. CONNELL ◽  
CHARLES S. HANES
Keyword(s):  
Carboxylic Acid ◽  
Pyrrolidone Carboxylic Acid

Removal of pyrrolidone carboxylic acid: An HPLC study on a new mammalian gastrin

1982 ◽  
Vol 3 (1) ◽  
pp. 69
Author(s):  
R. Dimaline ◽  
J. Reeve
Keyword(s):  
Carboxylic Acid ◽  
Pyrrolidone Carboxylic Acid ◽  
Hplc Study

Synthesis of novel quinolone and quinoline-2-carboxylic acid (4-morpholin-4-yl-phenyl)amides: A late-stage diversification approach to potent 5HT1B antagonists

2007 ◽  
Vol 15 (2) ◽  
pp. 939-950 ◽  
Author(s):  
Carey L. Horchler ◽  
John P. McCauley ◽  
James E. Hall ◽  
Dean H. Snyder ◽  
W. Craig Moore ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Late Stage

Weak acid-catalyzed pyrrolidone carboxylic acid formation from glutamine during solid phase peptide synthesis

2009 ◽  
Vol 19 (1) ◽  
pp. 88-93 ◽  
Author(s):  
RICHARD D. DIMARCHI ◽  
JAMES P. TAM ◽  
STEPHEN B.H. KENT ◽  
R.B. MERRIFIELD
Keyword(s):  
Carboxylic Acid ◽  
Peptide Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Weak Acid ◽  
Acid Formation ◽  
Pyrrolidone Carboxylic Acid ◽  
Acid Catalyzed

scholarly journals Studies on Metabolism of Pyrrolidone Carboxylic Acid in Bacteria

1965 ◽  
Vol 29 (5) ◽  
pp. 395-402 ◽  
Author(s):  
Yoshio KAWAI ◽  
Yasuo KAWAI ◽  
Teijiro UEMURA
Keyword(s):  
Carboxylic Acid ◽  
Pyrrolidone Carboxylic Acid

scholarly journals Practical and Regioselective Synthesis of C4-Alkylated Pyridines

2021 ◽  
Author(s):  
jin choi ◽  
Gabriele Laudadio ◽  
Edouard Godineau ◽  
Phil Baran
Keyword(s):  
Carboxylic Acid ◽  
Late Stage ◽  
Building Blocks ◽  
Regioselective Synthesis ◽  
Heterocyclic Chemistry ◽  
Blocking Group ◽  
Functionalized Materials

The direct position-selective C–4 alkylation of pyridines has been a longstanding challenge in heterocyclic chemistry, particularly from pyridine itself. Historically this has been addressed using pre-functionalized materials to avoid overalkylation and mixtures of regioisomers. This study reports the invention of a simple maleate-derived blocking group for pyridines that enables exquisite control for Minisci-type decarboxylative alkylation at C–4 that allows for inexpensive access to these valuable building blocks. The method is employed on a variety of different pyridines and carboxylic acid alkyl donors, is operationally simple, scalable, and is applied to access known structures in a rapid and inexpensive fashion. Finally, this work points to an interesting strategic departure for the use of Minisci chemistry at the earliest possible stage (native pyridine) rather than current dogma that almost exclusively employs Minisci as a late-stage functionalization technique.

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