HPLC Determination of Enantiomeric Purity of Protected Amino Acid Derivatives Used in Peptide Synthesis

1994 ◽  
Vol 17 (13) ◽  
pp. 2759-2775 ◽  
Author(s):  
Gy. Szókán ◽  
Sz. Hadfi ◽  
K. Krizsán ◽  
A. Liembeck ◽  
I. Krecz ◽  
...  
Keyword(s):  
Amino Acid ◽  
Peptide Synthesis ◽  
Enantiomeric Purity ◽  
Hplc Determination ◽  
Amino Acid Derivatives ◽  
Protected Amino Acid

ChemInform Abstract: Urethane-Protected Amino Acid N-Carboxy Anhydrides and Their Use in Peptide Synthesis.

ChemInform ◽  
2010 ◽  
Vol 22 (2) ◽  
pp. no-no
Author(s):  
W. D. FULLER ◽  
M. P. COHEN ◽  
M. SHABANKAREH ◽  
R. K. BLAIR ◽  
M. GOODMAN ◽  
...  
Keyword(s):  
Amino Acid ◽  
Peptide Synthesis ◽  
Protected Amino Acid

Solution phase peptide synthesis with ferrocenyl amino acid derivatives

2001 ◽  
Vol 637-639 ◽  
pp. 349-355 ◽  
Author(s):  
Jan Sehnert ◽  
Alexandra Hess ◽  
Nils Metzler-Nolte
Keyword(s):  
Amino Acid ◽  
Peptide Synthesis ◽  
Solution Phase ◽  
Amino Acid Derivatives

N-Methylamino acids in peptide synthesis. VII. Studies on the enantiomeric purity of N-methylamino acids prepared by various procedures

1977 ◽  
Vol 55 (5) ◽  
pp. 916-921 ◽  
Author(s):  
S. T. Cheung ◽  
N. Leo Benoiton
Keyword(s):  
Amino Acid ◽  
Methyl Iodide ◽  
Peptide Synthesis ◽  
Liquid Ammonia ◽  
Silver Oxide ◽  
Sodium Hydride ◽  
Enantiomeric Purity ◽  
Amino Acid Analyzer ◽  
Pure Compounds ◽  
Optically Pure

The enantiomeric purity of N-methylamino acids and their derivatives obtained by various procedures has been examined by analysis with an amino-acid analyzer of the diastereomeric lysyl dipeptides formed by coupling them with a lysyl derivative. N-Benzyloxycarbonyl, and N-tert-butyloxycarbonyl,N-methylamino acids obtained by methylation of the parent derivative using sodium hydride and methyl iodide, and N-methylamino acids obtained by methylation of the p-toluenesulfonylamino acid followed by treatment with sodium in liquid ammonia, are optically pure. Compounds obtained by other procedures which include reductive alkylations or the use of silver oxide – methyl iodide are generally not optically pure.

Simultaneous two-dimensional HPLC determination of free d-serine and d-alanine in the brain and periphery of mutant rats lacking d-amino-acid oxidase

2011 ◽  
Vol 879 (29) ◽  
pp. 3184-3189 ◽  
Author(s):  
Yurika Miyoshi ◽  
Kenji Hamase ◽  
Tadashi Okamura ◽  
Ryuichi Konno ◽  
Noriyuki Kasai ◽  
...  
Keyword(s):  
Amino Acid ◽  
Hplc Determination ◽  
Acid Oxidase ◽  
Two Dimensional ◽  
Amino Acid Oxidase ◽  
The Brain

N-Methylamino acids in peptide synthesis. V. The synthesis of N-tert-butyloxycarbonyl, N-methylamino acids by N-methylation

1977 ◽  
Vol 55 (5) ◽  
pp. 906-910 ◽  
Author(s):  
S. T. Cheung ◽  
N. Leo Benoiton
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Methyl Iodide ◽  
Peptide Synthesis ◽  
Room Temperature ◽  
Sodium Hydride ◽  
Amino Acid Derivatives ◽  
Enantiomerically Pure ◽  
Neutral Amino Acids ◽  
Related Data

The preparation of enantiomerically pure N-tert-butyloxycarbonyl,N-methylamino acids by N-methylation of the parent amino acid derivatives using sodium hydride and methyl iodide in tetrahydrofuran at room temperature is described for neutral amino acids including O-benzyl-protected threonine and tyrosine. Methylation of the O-benzylserine derivative under these conditions gives the N-methyldehydroalanine derivative. The β-elimination is completely suppressed, giving the corresponding N-methylserine derivative when the reaction is carried out at 5 °C. Other related data on N-methylation and N-methylamino acid derivatives are presented.

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