Solid-phase synthesis of linear and cyclic peptides containing a calix[4]arene amino acid

2009 ◽  
Vol 50 (26) ◽  
pp. 3450-3453 ◽  
Author(s):  
Laura Baldini ◽  
Francesco Sansone ◽  
Federico Scaravelli ◽  
Chiara Massera ◽  
Alessandro Casnati ◽  
...  
Keyword(s):  
Amino Acid ◽  
Cyclic Peptides ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Phase Synthesis

Oxytocin analogues with non-coded amino acid residues in position 8: [8-Neopentylglycine]oxytocin and [8-cycloleucine]oxytocin

1987 ◽  
Vol 52 (9) ◽  
pp. 2317-2325 ◽  
Author(s):  
Jan Hlaváček ◽  
Jan Pospíšek ◽  
Jiřina Slaninová ◽  
Walter Y. Chan ◽  
Victor J. Hruby
Keyword(s):  
Amino Acid ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
The Other ◽  
Amino Acid Residues ◽  
Phase Synthesis ◽  
Other Hand ◽  
Fragment Condensation

[8-Neopentylglycine]oxytocin (II) and [8-cycloleucine]oxytocin (III) were prepared by a combination of solid-phase synthesis and fragment condensation. Both analogues exhibited decreased uterotonic potency in vitro, each being about 15-30% that of oxytocin. Analogue II also displayed similarly decreased uterotonic potency in vivo and galactogogic potency. On the other hand, analogue III exhibited almost the same potency as oxytocin in the uterotonic assay in vivo and in the galactogogic assay.

Comparison of the Potency of 8-L-Arginine, 8-D-Arginine and 8-D-Homoarginine Vasopressin Analogs with Substituted Phenylalanine in Position 2

1994 ◽  
Vol 59 (6) ◽  
pp. 1439-1450 ◽  
Author(s):  
Miroslava Žertová ◽  
Jiřina Slaninová ◽  
Zdenko Procházka
Keyword(s):  
Amino Acid ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Basic Amino Acid ◽  
The Other ◽  
Side Chain ◽  
Inhibitory Potency ◽  
Phase Synthesis ◽  
Other Hand ◽  
Order Of Magnitude

An analysis of the uterotonic potencies of all analogs having substituted L- or D-tyrosine or -phenylalanine in position 2 and L-arginine, D-arginine or D-homoarginine in position 8 was made. The series of analogs already published was completed by the solid phase synthesis of ten new analogs having L- or D-Phe, L- or D-Phe(2-Et), L- or D-Phe(2,4,6-triMe) or D-Tyr(Me) in position 2 and either L- or D-arginine in position 8. All newly synthesized analogs were found to be uterotonic inhibitors. Deamination increases both the agonistic and antagonistic potency. In the case of phenylalanine analogs the change of configuration from L to D in position 2 enhances the uterotonic inhibition for more than 1 order of magnitude. The L to D change in position 8 enhances the inhibitory potency negligibly. Prolongation of the side chain of the D-basic amino acid in position 8 seems to decrease slightly the inhibitory potency if there is L-substituted amino acid in position 2. On the other hand there is a tendency to the increase of the inhibitory potency if there is D-substituted amino acid in position 2.

scholarly journals Solid-phase synthesis of biaryl cyclic peptides containing a histidine-tyrosine linkage

Tetrahedron ◽  
2019 ◽  
Vol 75 (18) ◽  
pp. 2625-2636 ◽  
Author(s):  
Iteng Ng-Choi ◽  
Àngel Oliveras ◽  
Marta Planas ◽  
Lidia Feliu
Keyword(s):  
Cyclic Peptides ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Phase Synthesis

A novel, convenient, three-dimensional orthogonal strategy for solid-phase synthesis of cyclic peptides

1993 ◽  
Vol 34 (10) ◽  
pp. 1549-1552 ◽  
Author(s):  
Steven A. Kates ◽  
Nuria A. Solé ◽  
Charles R. Johnson ◽  
Derek Hudson ◽  
George Barany ◽  
...  
Keyword(s):  
Cyclic Peptides ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Three Dimensional ◽  
Phase Synthesis

ChemInform Abstract: Homodetic Cyclic Peptides via Solid-Phase Synthesis

ChemInform ◽  
2010 ◽  
Vol 31 (28) ◽  
pp. no-no
Author(s):  
Christopher Blackburn ◽  
Steven A. Kates
Keyword(s):  
Cyclic Peptides ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Phase Synthesis

Amino acid derived sulfonamide hydroxamates as inhibitors of procollagen C-Proteinase: solid-Phase synthesis of ornithine analogues

2001 ◽  
Vol 11 (16) ◽  
pp. 2085-2088 ◽  
Author(s):  
Sharon M. Dankwardt ◽  
Robert L. Martin ◽  
Christine S. Chan ◽  
Harold E. Van Wart ◽  
Keith A.M. Walker ◽  
...  
Keyword(s):  
Amino Acid ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Phase Synthesis

Solid-Phase Synthesis of Acyclic and Cyclic Amino Acid Derived Urea Peptidomimetics Using Phoxime Resin†

1999 ◽  
Vol 1 (2) ◽  
pp. 163-172 ◽  
Author(s):  
Yoshitomo Hamuro ◽  
William J. Marshall ◽  
Mark A. Scialdone
Keyword(s):  
Amino Acid ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Phase Synthesis

Parallel Solid-Phase Synthesis of Partially Modified Retro and Retro-Inverso ψ[NHCH(CF3)]-Gly Peptides

2002 ◽  
Vol 67 (9) ◽  
pp. 1305-1319 ◽  
Author(s):  
Monica Sani ◽  
Pierfrancesco Bravo ◽  
Alessandro Volonterio ◽  
Matteo Zanda
Keyword(s):  
Amino Acid ◽  
Mild Condition ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Peptide Bond ◽  
Amino Acid Esters ◽  
Phase Synthesis ◽  
Acid Esters

The parallel solid-phase synthesis of small libraries of molecules belonging to a novel class of retro and retro-inverso peptides having a ψ[NHCH(CF3)] surrogate of the conventional retro-peptide bond (NH-CO) has been accomplished. Key step for the synthesis of the -NHCH(CF3)- unit is a Michael-type N-addition of resin bound α-amino acid esters H-AA1-OWang (1), dipeptide H-Val-Gly-OWang (8), and tripeptide H-Val-Val-Ala-OWang (12) to (S)-3-(E-enoyl)-1,3-oxazolidin-2-one (3), which took place very effectively under mild condition. Chemoselective exocyclic oxazolidinone cleavage, followed by parallel couplings of the resulting polymer-bound pseudopeptides WangO-AA1-ψ[NHCH(CF3)]-Gly-OH (5), WangO-Gly-Val-ψ[NHCH(CF3)]-Gly-OH (10), and WangO-Ala-Val-Val-ψ[NHCH(CF3)]-Gly-OH (14) with different α-amino acid esters afforded, after release from the resin, a representative set of ψ[NHCH(CF3)] retro and retro-inverso tripeptides HO-AA1-ψ[NHCH(CF3)]-Gly-AA2-OX1 (7), tetrapeptides HO-Gly-Val-ψ[NHCH(CF3)]-Gly-AA3-OX2 (11), and pentapeptides HO-Ala-Val-Val-ψ[NHCH(CF3)]-Gly-AA4-OX3 (15), respectively, with good to excellent purity in all cases.

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