Test for racemization in model peptide synthesis by direct chromatographic separation of diastereomers of the tetrapeptide leucylalanylglycylvaline

1978 ◽  
Vol 50 (1) ◽  
pp. 155-159 ◽  
Author(s):  
S. B. H. Kent ◽  
A. R. Mitchell ◽  
G. Barany ◽  
R. B. Merrifield
Keyword(s):  
Peptide Synthesis ◽  
Chromatographic Separation ◽  
Model Peptide ◽  
Separation Of Diastereomers

A Rapid and Simple Chromatographic Separation of Diastereomers of Silibinin and Their Oxidation to Produce 2,3-Dehydrosilybin Enantiomers in an Optically Pure Form

Planta Medica ◽  
2013 ◽  
Vol 79 (12) ◽  
pp. 1077-1080 ◽  
Author(s):  
Giovanni Di Fabio ◽  
Valeria Romanucci ◽  
Cinzia Di Marino ◽  
Lorenzo De Napoli ◽  
Armando Zarrelli
Keyword(s):  
Chromatographic Separation ◽  
Pure Form ◽  
Separation Of Diastereomers ◽  
Optically Pure

scholarly journals Synthesis of enantiomerically pure (2S,3S)-5,5,5-trifluoroisoleucine and (2R,3S)-5,5,5-trifluoro-allo-isoleucine

2013 ◽  
Vol 9 ◽  
pp. 2009-2014 ◽  
Author(s):  
Holger Erdbrink ◽  
Elisabeth K Nyakatura ◽  
Susanne Huhmann ◽  
Ulla I M Gerling ◽  
Dieter Lentz ◽  
...  
Keyword(s):  
Peptide Synthesis ◽  
Stereoselective Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Model Peptide ◽  
Enantiomerically Pure ◽  
Helix Propensity ◽  
Α Helix

A practical route for the stereoselective synthesis of (2S,3S)-5,5,5-trifluoroisoleucine (L-5-F3Ile) and (2R,3S)-5,5,5-trifluoro-allo-isoleucine (D-5-F3-allo-Ile) was developed. The hydrophobicity of L-5-F3Ile was examined and it was incorporated into a model peptide via solid phase peptide synthesis to determine its α-helix propensity. The α-helix propensity of 5-F3Ile is significantly lower than Ile, but surprisingly high when compared with 4’-F3Ile.

scholarly journals Total Chemical Synthesis of a Heterodimeric Interchain Bis-Lactam-Linked Peptide: Application to an Analogue of Human Insulin-Like Peptide 3

2013 ◽  
Vol 2013 ◽  
pp. 1-8 ◽  
Author(s):  
John Karas ◽  
Fazel Shabanpoor ◽  
Mohammed Akhter Hossain ◽  
James Gardiner ◽  
Frances Separovic ◽  
...  
Keyword(s):  
Chemical Synthesis ◽  
Peptide Synthesis ◽  
Disulfide Bonds ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Protecting Groups ◽  
Model Peptide ◽  
Design Elements

Nonreducible cystine isosteres represent important peptide design elements in that they can maintain a near-native tertiary conformation of the peptide while simultaneously extending the in vitro and in vivo half-life of the biomolecule. Examples of these cystine mimics include dicarba, diselenide, thioether, triazole, and lactam bridges. Each has unique physicochemical properties that impact upon the resulting peptide conformation. Each also requires specific conditions for its formation via chemical peptide synthesis protocols. While the preparation of peptides containing two lactam bonds within a peptide is technically possible and reported by others, to date there has been no report of the chemical synthesis of a heterodimeric peptide linked by two lactam bonds. To examine the feasibility of such an assembly, judicious use of a complementary combination of amine and acid protecting groups together with nonfragment-based, total stepwise solid phase peptide synthesis led to the successful preparation of an analogue of the model peptide, insulin-like peptide 3 (INSL3), in which both of the interchain disulfide bonds were replaced with a lactam bond. An analogue containing a single disulfide-substituted interchain lactam bond was also prepared. Both INSL3 analogues retained significant cognate RXFP2 receptor binding affinity.

scholarly journals Comparative Investigation of the Cleavage Step in the Synthesis of Model Peptide Resins: Implications for Nα-9-Fluorenylmethyloxycarbonyl-Solid Phase Peptide Synthesis

2007 ◽  
Vol 55 (3) ◽  
pp. 468-470 ◽  
Author(s):  
Guita Nicolaewsky Jubilut ◽  
Eduardo Maffud Cilli ◽  
Edson Crusca, Jr. ◽  
Elias Horacio Silva ◽  
Yoshio Okada ◽  
...  
Keyword(s):  
Peptide Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Comparative Investigation ◽  
Model Peptide ◽  
Cleavage Step
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