Amino acids and peptides. XXVIII. A new synthesis of .ALPHA.-amino acid derivatives by alkylation of Schiff bases derived from glycine and alanine.

TOMEI OGURI; TAKAYUKI SHIOIRI; SHUNICHI YAMADA

doi:10.1248/cpb.25.2287

Amino acids and peptides. XXVIII. A new synthesis of .ALPHA.-amino acid derivatives by alkylation of Schiff bases derived from glycine and alanine.

Chemical and Pharmaceutical Bulletin ◽

10.1248/cpb.25.2287 ◽

1977 ◽

Vol 25 (9) ◽

pp. 2287-2291 ◽

Cited By ~ 28

Author(s):

TOMEI OGURI ◽

TAKAYUKI SHIOIRI ◽

SHUNICHI YAMADA

Keyword(s):

Amino Acids ◽

Amino Acid ◽

Schiff Bases ◽

Amino Acid Derivatives ◽

New Synthesis ◽

Alpha Amino Acid

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ChemInform Abstract: AMINO ACIDS AND PEPTIDES. XXVIII. A NEW SYNTHESIS OF α-AMINO ACID DERIVATIVES BY ALKYLATION OF SCHIFF BASES DERIVED FROM GLYCINE AND ALANINE

Chemischer Informationsdienst ◽

10.1002/chin.197802332 ◽

1978 ◽

Vol 9 (2) ◽

Author(s):

T. OGURI ◽

T. SHIOIRI ◽

S. YAMADA

Keyword(s):

Amino Acids ◽

Amino Acid ◽

Schiff Bases ◽

Amino Acid Derivatives ◽

New Synthesis

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Amino acids and peptides. XXIX. A new efficient asymmetric synthesis of .ALPHA.-amino acid derivatives with recycle of a chiral reagent - asymmetric alkylation of a chiral Schiff base from glycine.

Chemical and Pharmaceutical Bulletin ◽

10.1248/cpb.26.803 ◽

1978 ◽

Vol 26 (3) ◽

pp. 803-808 ◽

Cited By ~ 74

Author(s):

TOMEI OGURI ◽

NOBUTAKA KAWAI ◽

TAKAYUKI SHIOIRI ◽

SHUNICHI YAMADA

Keyword(s):

Amino Acids ◽

Schiff Base ◽

Amino Acid ◽

Asymmetric Synthesis ◽

Amino Acid Derivatives ◽

Asymmetric Alkylation ◽

Chiral Reagent ◽

Chiral Schiff Base ◽

Alpha Amino Acid

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Reaction of .beta.-hydroxy .alpha.-amino acid derivatives with (diethylamino)sulfur trifluoride (DAST). Synthesis of .beta.-fluoro .alpha.-amino acids

The Journal of Organic Chemistry ◽

10.1021/jo00230a033 ◽

1987 ◽

Vol 52 (21) ◽

pp. 4804-4810 ◽

Cited By ~ 37

Author(s):

Sunil V. Pansare ◽

John C. Vederas

Keyword(s):

Amino Acids ◽

Amino Acid ◽

Amino Acid Derivatives ◽

Alpha Amino Acid

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Optical Rotatory Dispersion Studies. XLVI. Stereochemical Assignments through Anomalous Rotatory Dispersion Curves of alpha-Amino Acid Derivatives. 3-Phenyl-2-thiohydantoins and N-Thionocarbethoxy Amino Acids.

Acta Chemica Scandinavica ◽

10.3891/acta.chem.scand.15-0903 ◽

1961 ◽

Vol 15 ◽

pp. 903-912 ◽

Cited By ~ 30

Author(s):

Carl Djerassi ◽

Kjell Undheim ◽

R. C. Sheppard ◽

W. G. Terry ◽

Berndt Sjöberg ◽

...

Keyword(s):

Amino Acids ◽

Amino Acid ◽

Dispersion Curves ◽

Optical Rotatory Dispersion ◽

Rotatory Dispersion ◽

Amino Acid Derivatives ◽

Optical Rotatory ◽

Alpha Amino Acid

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Faculty Opinions recommendation of Catalytic enantio- and diastereoselective aldol reactions of glycine-derived silicon enolate with aldehydes: an efficient approach to the asymmetric synthesis of anti-beta-hydroxy-alpha-amino acid derivatives.

Faculty Opinions – Post-Publication Peer Review of the Biomedical Literature ◽

10.3410/f.1020519.232639 ◽

2004 ◽

Author(s):

Carlos F Barbas

Keyword(s):

Amino Acid ◽

Asymmetric Synthesis ◽

Aldol Reactions ◽

Amino Acid Derivatives ◽

Efficient Approach ◽

Alpha Amino Acid

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Faculty Opinions recommendation of Deorphanization of GPRC6A: a promiscuous L-alpha-amino acid receptor with preference for basic amino acids.

Faculty Opinions – Post-Publication Peer Review of the Biomedical Literature ◽

10.3410/f.1024356.287883 ◽

2005 ◽

Author(s):

Joseph Heitman

Keyword(s):

Amino Acids ◽

Amino Acid ◽

Acid Receptor ◽

Basic Amino Acids ◽

Alpha Amino Acid

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ChemInform Abstract: Catalytic Asymmetric Synthesis of Functionalized α,α-Disubstituted α-Amino Acid Derivatives from Racemic Unprotected α-Amino Acids via in situ Generated Azlactones.

ChemInform ◽

10.1002/chin.201242200 ◽

2012 ◽

Vol 43 (42) ◽

pp. no-no

Author(s):

Manuel Weber ◽

Wolfgang Frey ◽

Rene Peters

Keyword(s):

Amino Acids ◽

Amino Acid ◽

Asymmetric Synthesis ◽

Amino Acid Derivatives ◽

Catalytic Asymmetric Synthesis ◽

Catalytic Asymmetric

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Cyclization of N-oxalyl-.alpha.-amino acid derivatives

The Journal of Organic Chemistry ◽

10.1021/jo01274a078 ◽

1968 ◽

Vol 33 (10) ◽

pp. 3980-3983 ◽

Cited By ~ 3

Author(s):

Walter Hearn ◽

Jorge Medina-Castro

Keyword(s):

Amino Acid ◽

Amino Acid Derivatives ◽

Alpha Amino Acid

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Enantioselective synthesis of α-alkenyl α-amino acids via N–H insertion reactions

Chemical Science ◽

10.1039/c5sc03558a ◽

2016 ◽

Vol 7 (2) ◽

pp. 1104-1108 ◽

Cited By ~ 27

Author(s):

Jun-Xia Guo ◽

Ting Zhou ◽

Bin Xu ◽

Shou-Fei Zhu ◽

Qi-Lin Zhou

Keyword(s):

Amino Acids ◽

Amino Acid ◽

Enantioselective Synthesis ◽

Insertion Reaction ◽

Amino Acid Derivatives ◽

Insertion Reactions ◽

Phosphoric Acids

A new highly enantioselective route to α-alkenyl α-amino acid derivatives using a N–H insertion reaction of vinyldiazoacetates and tert-butyl carbamate cooperatively catalyzed by achiral dirhodium(ii) carboxylates and chiral spiro phosphoric acids was developed.

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Synthesis of New β-Amino Acids via 5-Oxazolidinones and the Arndt - Eistert Procedure

Australian Journal of Chemistry ◽

10.1071/ch05199 ◽

2005 ◽

Vol 58 (11) ◽

pp. 778 ◽

Cited By ~ 13

Author(s):

Andrew B. Hughes ◽

Brad E. Sleebs

Keyword(s):

Amino Acids ◽

Amino Acid ◽

Reductive Cleavage ◽

High Yield ◽

Amino Acid Derivatives ◽

Peptide Therapeutics

N-Methyl β-amino acids are potentially useful amino acid derivatives for incorporation in lead peptide therapeutics. The syntheses of five such compounds are presented. Their synthesis via 6-oxazinanones was low yielding. Alternatively, reductive cleavage of a 5-oxazolidinone gave the N-methyl α-amino acid, which was then homologated via an Arndt–Eistert procedure in high yield to give the N-methyl β-amino acid.

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