scholarly journals Development of the Schedule for Multiple Parallel “Difficult” Peptide Synthesis on Pins

2013 ◽  
Vol 2013 ◽  
pp. 1-9 ◽  
Author(s):  
Ekaterina F. Kolesanova ◽  
Maxim A. Sanzhakov ◽  
Oleg N. Kharybin

Unified schedule for multiple parallel solid-phase synthesis of so-called “difficult” peptides on polypropylene pins was developed. Increase in the efficiency of 9-fluorenyl(methoxycarbonyl) N-terminal amino-protecting group removal was shown to have a greater influence on the accuracy of the “difficult” peptide synthesis than the use of more efficient amino acid coupling reagents such as aminium salts. Hence the unified schedule for multiple parallel solid-phase synthesis of “difficult” peptides included the procedure for N-terminal amino group deprotection modified by applying a more efficient reagent for the deprotection and the standard procedure of amino acid coupling by carbodiimide method with an additional coupling using aminium salts, if necessary. Amino acid coupling with the help of carbodiimide allows to follow the completeness of the coupling via the bromophenol blue indication, thus providing the accuracy of the synthesis and preventing an overexpenditure of expensive reagents. About 100 biotinylated hepatitis C virus envelope protein fragments, most of which represented “difficult” peptides, were successfully obtained by synthesis on pins with the help of the developed unified schedule.

Synlett ◽  
2017 ◽  
Vol 29 (10) ◽  
pp. 1289-1292 ◽  
Author(s):  
Pablo Rivera-Fuentes ◽  
Alina Tirla ◽  
Moritz Hansen

Cyclic disulfides, such as asparagusic acid, enhance the uptake of a variety of cargoes into live cells. Here, we report a robust and scalable synthesis of an asparagusic acid modified lysine. This amino acid can be used in solid-phase peptide synthesis. We confirmed that incorporation of this building block into the sequence of a peptide increases its cellular uptake substantially.


Author(s):  
Javier Eduardo García Castañeda ◽  
Cristian Francisco Vergel Galeano ◽  
Zuly Jenny Rivera Monroy ◽  
Javier Eduardo Rosas Pérez

<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>


1987 ◽  
Vol 52 (9) ◽  
pp. 2317-2325 ◽  
Author(s):  
Jan Hlaváček ◽  
Jan Pospíšek ◽  
Jiřina Slaninová ◽  
Walter Y. Chan ◽  
Victor J. Hruby

[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.


1994 ◽  
Vol 59 (6) ◽  
pp. 1439-1450 ◽  
Author(s):  
Miroslava Žertová ◽  
Jiřina Slaninová ◽  
Zdenko Procházka

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.


Synlett ◽  
2017 ◽  
Vol 28 (15) ◽  
pp. 1956-1960 ◽  
Author(s):  
Shugo Tsuda ◽  
Taku Yoshiya ◽  
Tsuyoshi Uemura ◽  
Masayoshi Mochizuki ◽  
Hideki Nishio

Based on the structure of Dawson’s 3,4-diaminobenzoic acid (Dbz) linker designed for Fmoc solid-phase peptide-thioester synthesis, the 4-amino-3-nitrobenzoic acid [Dbz(NO2)] linker was developed for microwave-assisted synthesis. The Dbz(NO2) linker can be readily converted into the Dbz linker by on-resin reduction with SnCl2 after construction of the protected peptide resin. Although epimerization of C-terminal amino acid restricts the use of Dbz(NO2) linker to the synthesis of peptide-Gly-thioester, use of this linker can prevent side reactions that arise when Dbz or Dbz(Aloc) linkers are used in the microwave-assisted synthesis of Gly-rich peptides.


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 ◽  
...  

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