ChemInform Abstract: PEPTIDE SYNTHESIS. PART 2. PROCEDURES FOR SOLID-PHASE SYNTHESIS USING Nα-FLUORENYLMETHOXYCARBONYL AMINO ACIDS ON POLYAMIDE SUPPORTS. SYNTHESIS OF SUBSTANCE P AND OF ACYL CARRIER PROTEIN 65-74 DECAPEPTIDE

1981 ◽  
Vol 12 (20) ◽  
Author(s):  
E. ATHERTON ◽  
C. J. LOGAN ◽  
R. C. SHEPPARD
Keyword(s):  
Amino Acids ◽  
Substance P ◽  
Peptide Synthesis ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Acyl Carrier Protein ◽  
Carrier Protein ◽  
Phase Synthesis

Solid-Phase Synthesis of Peptides via a,β-Unsaturated Amino Acids. Incorporation of the Amide Gronp in encZo-Positions

1981 ◽  
Vol 36 (10) ◽  
pp. 1345-1348 ◽  
Author(s):  
Kosaku Nöda ◽  
Erhard Gross
Keyword(s):  
Amino Acids ◽  
Peptide Synthesis ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Phase Synthesis ◽  
Unsaturated Amino Acids ◽  
Model Peptides

Abstract Dehydroalanine is introduced as pseudoprotecting group for the to-amide function of Asn and Gin in solid-phase peptide synthesis. Using Boc-X(Dha-NHMe)-OH (X = Asp or Glu), the model peptides, L-Leu-L-Asn-Gly-NH2 and L-Leu-Lr-Gln-Gly-NH2, were synthesized

scholarly journals Efficient Synthesis of Peptides with 4-Methylpiperidine as Fmoc Removal Reagent by Solid Phase Synthesis

2017 ◽  
Vol 58 (4) ◽  
Author(s):  
Javier Eduardo García Castañeda ◽  
Cristian Francisco Vergel Galeano ◽  
Zuly Jenny Rivera Monroy ◽  
Javier Eduardo Rosas Pérez
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Peptide Synthesis ◽  
Synthetic Peptides ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Amino Group ◽  
Efficient Synthesis ◽  
Phase Synthesis

<p>Solid phase peptide synthesis using the Fmoc/<em>t</em>-Bu strategy (SPPS-Fmoc/tBu) is the most widely used methodology for obtaining synthetic peptides. In this paper, we evaluate the viability of using 4-methylpiperidine as a reagent for deprotection of the amino acid alpha amino group in SPPS-Fmoc/tBu. For this purpose, the peptide (RRWQWRMKKLG) was simultaneously synthesized using 4-methylpiperidine or piperidine for Fmoc removal reagent. The obtained products had similar purities and yields. Finally, 21 peptides were synthesized using 4-methylpiperidine. Our results suggest that is possible to obtain synthetic peptides efficiently by the strategy SPPS-Fmoc/tBu when 4-methylpiperidine was used as reagent to remove Fmoc groups N-alpha protected amino acids.</p>

The Boc/Solid Phase Synthesis of Glu-Abu(P)-Leu

1992 ◽  
Vol 45 (10) ◽  
pp. 1765 ◽  
Author(s):  
JW Perich ◽  
EC Reynolds
Keyword(s):  
Amino Acids ◽  
Peptide Synthesis ◽  
Trifluoroacetic Acid ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Hydrogen Bromide ◽  
Solid Phase Peptide Synthesis ◽  
Polymer Support ◽  
Methyl Groups ◽  
Phase Synthesis

The synthesis of the 4-phosphono-2-aminobutanoyl-containing tripeptide , H- Glu -Abu(P)- Leu-OH.CF3C02H was accomplished by the use of Boc-Abu(PO3Me2)-OH in Boc /solid phase peptide synthesis. Peptide synthesis was performed by using Boc-Leu-polystyrene as the polymer support with the peptide assembled by the use of 1H-benzotriazol-1-yloxytris(pyrro1idin-1-yl) phosphonium hexafluorophosphate ( PyBOPR ) for the coupling of Boc amino acids and 50% CF3C02H/CH2C12 for cleavage of the Boc group from the Boc -peptide after each coupling cycle. The protected peptide was cleaved from the polymer support by hydrogen bromide in trifluoroacetic acid and final cleavage of the methyl groups from Glu-Abu(PO2Me2)-Leu was effected by silylitic treatment with 30% bromotrimethylsilane in acetonitrile.

Vasopressin and oxytocin analogs with interchanged sequence of amino acids in positions 7 and 8. synthesis and biological effects

1981 ◽  
Vol 46 (9) ◽  
pp. 2136-2139 ◽  
Author(s):  
Ivo Bláha ◽  
Viktor Krchňák ◽  
Milan Zaoral
Keyword(s):  
Amino Acids ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Biological Effects ◽  
Free Flow ◽  
Protecting Groups ◽  
Pressor Effect ◽  
Phase Synthesis ◽  
Antidiuretic Effect

p-Toluenesulfonyl-S-benzylcysteinyl-tyrosyl-phenylalanyl-glutaminyl-asparaginyl-S-benzylcysteinyl-NG-p-toluenesulfanylarginyl-prolyl-glycineamide (I) and S-benzylcysteinyl-tyrosyl-isoleucyl-glutaminyl-asparaginyl-S-benzylcysteinyl-leucyl-prolyl-glycine amide (III) were prepared by solid phase synthesis. After removal of the protecting groups, closure of the disulfide ring, and purification by continuous free-flow electrophoresis [arginine7, proline8]vasopressin (II) and [leucine7, proline8]oxytocin (IV) were obtained. The antidiuretic effect of II is markedly higher than its pressor effect; IV possesses c. 6% of the uterotonic and c. 10% of the galactogogous effect of oxytocin.

Solid Phase Synthesis of a Somatostatin Amide Analogue Using Acid Labile t-Bumeoc Protection and an Acid Labile Anchor Group

1992 ◽  
Vol 57 (8) ◽  
pp. 1707-1718
Author(s):  
Wolfgang Voelter ◽  
Gerhard Breipohl ◽  
Chryssa Tzougraki ◽  
Eveline Jungfleisch-Turgut
Keyword(s):  
Amino Acids ◽  
Acetic Acid ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Somatostatin Analogue ◽  
Phase Synthesis ◽  
Anchor Group ◽  
Amide Form ◽  
Polystyrene Resin ◽  
Acid Labile

The solid phase synthesis of an amidated somatostatin analogue based on the principle of differentiated acidolysis is described. The acid labile and smoothly cleavable t-Bumeoc moiety (1% TFA/DCM) is used for temporary Nα-protection of D- and L-amino acids and [4-[[[9H-fluoren-9-yl-methoxycarbonyl]amino](4-methoxyphenyl)methyl]-2-methylphenoxy]acetic acid, attached to an aminomethylated polystyrene resin is used as acid sensitive linker of the solid carrier which releases the peptide in its amide form by treatment with TFA. Its preparation is described in detail.

Festphasensynthese von Muramyldipeptiden an isomeren Trialkoxybenzylamin-Harzen / Solid Phase Synthesis of Muramyl Dipeptides on Isomeric Trialkoxybenzylamine Resins

1998 ◽  
Vol 53 (7) ◽  
pp. 753-764 ◽  
Author(s):  
Hans-Jürgen Kohlbaua ◽  
Jochen Tschakert ◽  
Raed A. Al-Qawasmeh ◽  
Tanveer Ahmad Nizamì ◽  
Abdul Malik ◽  
...  
Keyword(s):  
Amino Acids ◽  
Trifluoroacetic Acid ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Subsequent Treatment ◽  
Phase Synthesis ◽  
Merrifield Resin

Abstract New isomeric trialkoxybenzylamine resins are developed coupling phthalimidomethyl-3,5-dimethoxyphenols to the Merrifield resin, followed by subsequent treatment with hydrazine. The generated benzylamine function allows DCC coupling w ith the carboxyl function of amino acids and peptides which are removed as amides after treatment with trifluoroacetic acid. These new trialkoxybenzylamine resins allow expeditious syntheses of peptide amides and glycopeptide amides as is demonstrated for muramyl peptides and analogues.

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