Stepwise Automated Solid Phase Synthesis of Naturally Occurring Peptaibols Using FMOC Amino Acid Fluorides

1995 ◽  
Vol 60 (2) ◽  
pp. 405-410 ◽  
Author(s):  
Holger Wenschuh ◽  
Michael Beyermann ◽  
Hanka Haber ◽  
Joachim K. Seydel ◽  
Eberhard Krause ◽  
...  
Keyword(s):  
Amino Acid ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Phase Synthesis ◽  
Naturally Occurring ◽  
Amino Acid Fluorides ◽  
Acid Fluorides

Multiple solid phase synthesis via Fmoc-amino acid fluorides

1995 ◽  
Vol 36 (8) ◽  
pp. 1247-1250 ◽  
Author(s):  
Holger Wenschuh ◽  
Michael Beyermann ◽  
Sven Rothemund ◽  
Louis A. Carpino ◽  
Michael Bienert
Keyword(s):  
Amino Acid ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Phase Synthesis ◽  
Amino Acid Fluorides ◽  
Acid Fluorides

Stepwise solid phase synthesis of peptaibols using Fmoc-amino acid fluorides

Peptides 1994 ◽  
1995 ◽  
pp. 287-288
Author(s):  
H. Wenschuh ◽  
L. A. Carpino ◽  
F. Albericio ◽  
E. Krause ◽  
M. Beyermann ◽  
...  
Keyword(s):  
Amino Acid ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Phase Synthesis ◽  
Amino Acid Fluorides ◽  
Acid Fluorides

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 Processing of RNA Containing 8-Oxo-7,8-Dihydroguanosine (8-oxoG) by the Exoribonuclease Xrn-1

2021 ◽  
Vol 8 ◽  
Author(s):  
Cheyenne N. Phillips ◽  
Shawn Schowe ◽  
Conner J. Langeberg ◽  
Namoos Siddique ◽  
Erich G. Chapman ◽  
...  
Keyword(s):  
Secondary Structure ◽  
Conformational Changes ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Spatial Constraints ◽  
Phase Synthesis ◽  
Naturally Occurring ◽  
Processive Enzyme ◽  
Moving Band ◽  
Hydrolysis Of

Understanding how oxidatively damaged RNA is handled intracellularly is of relevance due to the link between oxidized RNA and the progression/development of some diseases as well as aging. Among the ribonucleases responsible for the decay of modified (chemically or naturally) RNA is the exonuclease Xrn-1, a processive enzyme that catalyzes the hydrolysis of 5′-phosphorylated RNA in a 5′→3′ direction. We set out to explore the reactivity of this exonuclease towards oligonucleotides (ONs, 20-nt to 30-nt long) of RNA containing 8-oxo-7,8-dihydroguanosine (8-oxoG), obtained via solid-phase synthesis. The results show that Xrn-1 stalled at sites containing 8-oxoG, evidenced by the presence of a slower moving band (via electrophoretic analyses) than that observed for the canonical analogue. The observed fragment(s) were characterized via PAGE and MALDI-TOF to confirm that the oligonucleotide fragment(s) contained a 5′-phosphorylated 8-oxoG. Furthermore, the yields for this stalling varied from app. 5–30% with 8-oxoG located at different positions and in different sequences. To gain a better understanding of the decreased nuclease efficiency, we probed: 1) H-bonding and spatial constraints; 2) anti-syn conformational changes; 3) concentration of divalent cation; and 4) secondary structure. This was carried out by introducing methylated or brominated purines (m1G, m6,6A, or 8-BrG), probing varying [Mg2+], and using circular dichroism (CD) to explore the formation of structured RNA. It was determined that spatial constraints imposed by conformational changes around the glycosidic bond may be partially responsible for stalling, however, the results do not fully explain some of the observed higher stalling yields. We hypothesize that altered π-π stacking along with induced H-bonding interactions between 8-oxoG and residues within the binding site may also play a role in the decreased Xrn-1 efficiency. Overall, these observations suggest that other factors, yet to be discovered/established, are likely to contribute to the decay of oxidized RNA. In addition, Xrn-1 degraded RNA containing m1G, and stalled mildly at sites where it encountered m6,6A, or 8-BrG, which is of particular interest given that the former two are naturally occurring modifications.

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

ChemInform Abstract: Solid-Phase Synthesis of a 36 Amino Acid O-Fucosyl-peptide with the Uncommon Thr-Fuc-Linkage

ChemInform ◽  
2010 ◽  
Vol 27 (16) ◽  
pp. no-no
Author(s):  
H. HIETTER ◽  
M. SCHULTZ ◽  
H. KUNZ
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

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
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