Solution Phase Synthesis of Glu-Abu(P)-Leu by Using Z-Abu(PO3Et2)-OH

1992 ◽  
Vol 45 (5) ◽  
pp. 919
Author(s):  
JW Perich ◽  
RM Valerio ◽  
RB Johns
Keyword(s):  
Solution Phase ◽  
Mixed Anhydride ◽  
Phase Synthesis ◽  
Solution Phase Synthesis

This paper describes the synthesis of the 2-amino-4-(phosphono)butanoyl-containing peptide H-Glu-Abu(P)-Leu-OH.CF3CO2H by the use of Z-Abu(PO3Et2)-OH for the solution phase synthesis of Boc-Glu(Obut)-Abu(PO3Et2)-Leu-Obut (mixed-anhydride method) followed by acidolytic cleavage of the t-butyl groups, and final removal of the ethyl groups from Glu- Abu(PO3Et2)-Leu by treatment with 10% bromotrimethylsilane in acetonitrile. Although silylitic cleavage of the peptide was facile, the slow dissolution of the peptide in the reaction solvent suggests that deprotection of the Abu(PO3.Et2) residue has not yet been optimized.

Synthesis of Casein-Related Peptides and Phosphopeptides. I. Solution-Phase Synthesis and 13C N.M.R.-Spectroscopy of the N-α-Acetyl Octapeptide N-Methylamide Corresponding to Region 14-21 of Bovine β-Casein A2

1987 ◽  
Vol 40 (2) ◽  
pp. 257 ◽  
Author(s):  
JW Perich ◽  
PF Alewood ◽  
RB Johns
Keyword(s):  
Solution Phase ◽  
Phase Method ◽  
Peptide Fragments ◽  
Mixed Anhydride ◽  
Phase Synthesis ◽  
Solution Phase Synthesis ◽  
Coupling Procedure ◽  
Fragment Condensation ◽  
High Yields ◽  
Solution Phase Method

The octapeptide, Ac-Glu-Ser-Leu-Ser-Ser-Ser-Glu-Glu-NHMe (I), was synthesized by the solution-phase method by using the mixed anhydride coupling procedure for the fragment condensation of the Nα-acetyl tripeptide, Ac-Glu(OBut)-Ser(But)-Leu-OH, with the pentapeptide N-methylamide hydrochloride, Cl.H2-Ser(But)-Ser(But)-Ser(But)-Glu(OBzl)-Glu(OBzl)-NHMe, followed by palladium-catalysed hydrogenolysis of Ac-Glu(OBut)-Ser(But)-Leu-Ser(But)-Ser(But)- Ser(But) Glu(OBzl)Glu(OBzl NHMe in trifluoroacetic acid. The synthesis of the two peptide fragments was accomplished in high yields and purity by using the repetitive excess mixed anhydride procedure and the isobutoxycarbonyl mixed anhydride of acetic acid for the rapid and high yielding N-acetylation of the tripeptide fragment. 13C n.m.r. spectroscopy was routinely used to monitor the efficiency of the coupling steps and to confirm the structure of octapeptide (1), signal assignments being possible for both the protected tri- and penta-peptides.

Solution phase synthesis of oligonucleotides by the phosphoramidite method using solid supported reagents

2005 ◽  
Author(s):  
François Morvan ◽  
Aude-Emmanuelle Navarro ◽  
Cécile Dueymes ◽  
Ilaria Adamo ◽  
Andreas Schoenberger ◽  
...  
Keyword(s):  
Solution Phase ◽  
Phase Synthesis ◽  
Solution Phase Synthesis

Polymer-Assisted Parallel Solution Phase Synthesis of Substituted Benzimidazoles.

ChemInform ◽  
2010 ◽  
Vol 33 (35) ◽  
pp. 123-123
Author(s):  
Young K. Yun ◽  
John A. Porco Jr. ◽  
Jeff Labadie
Keyword(s):  
Solution Phase ◽  
Phase Synthesis ◽  
Parallel Solution ◽  
Solution Phase Synthesis

Solution-phase synthesis of monodispersed SnTe nanocrystallites at room temperature

2003 ◽  
Vol 6 (2) ◽  
pp. 181-184 ◽  
Author(s):  
Changhua An ◽  
Kaibin Tang ◽  
Bin Hai ◽  
Guozhen Shen ◽  
Chunrui Wang ◽  
...  
Keyword(s):  
Room Temperature ◽  
Solution Phase ◽  
Phase Synthesis ◽  
Solution Phase Synthesis

Synthesis of O-Phosphotyrosine-Containing Peptides. II. Solution-Phase Synthesis of Asn-Glu-PTyr-Thr-Ala Through Methyl Phosphate Protection

1989 ◽  
Vol 42 (9) ◽  
pp. 1519 ◽  
Author(s):  
RM Valerio ◽  
JW Perich ◽  
EA Kitas ◽  
PF Alewood ◽  
RB Johns
Keyword(s):  
Trifluoroacetic Acid ◽  
Dimethyl Sulfide ◽  
Solution Phase ◽  
High Yield ◽  
Phase Synthesis ◽  
Rous Sarcoma ◽  
Naturally Occurring ◽  
Solution Phase Synthesis ◽  
Sarcoma Virus ◽  
Methyl Phosphate

The PTyr (O-phosphotyrosine) pentapeptide H-Asn-Glu-Tyr(PO3H2)-Thr-Ala-OH.HO2CCF3, which is a naturally occurring sequence from the autophosphorylated Rous sarcoma virus pp60V-SrC, was prepared in high yield by the use of Boc-Tyr(PO3Me2)-OH in the Boc mode of solution-phase peptide synthesis. The protected pentapeptide, Z-Asn-Glu(OBzl)-Tyr(PO3Me2)-Thr(Bzl)-Ala-OBzl, was deprotected by a two-stage procedure which involved initial palladium-catalysed hydrogenolysis followed by the removal of the phosphate methyl groups by the use of one of the following treatments: (A) 10% bromotrimethylsilane/acetonitrile, (B) 1 M bromotrimethylsilane/thioanisole in trifluoroacetic acid, or (C) trifluoromethanesulfonic acid/trifluoroacetic acid/dimethyl sulfide/m-cresol.

scholarly journals Solution-Phase Synthesis of a Highly Substituted Furan Library

2012 ◽  
Vol 14 (7) ◽  
pp. 403-414 ◽  
Author(s):  
Chul-Hee Cho ◽  
Feng Shi ◽  
Dai-Il Jung ◽  
Benjamin Neuenswander ◽  
Gerald H. Lushington ◽  
...  
Keyword(s):  
Solution Phase ◽  
Phase Synthesis ◽  
Solution Phase Synthesis
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