Racemisierungsfreie Peptidsynthese bei erhöhter Temperatur

Barlos, Kleomenis; Papaioannou, D.; Patrianakou, Stella; Tsegenidis, T.

doi:10.1002/jlac.198619861115

Cited by 34 publications

(13 citation statements)

References 4 publications

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“…The bulky methyl (trityl) and isobutyl groups surround the chiral Η-atom almost completely and do not allow the approach of a bulky base such as triethylamine. This favorable conformation explains why benzotriazolyl-esters of /V-trityl amino acids do not racemize even under extreme conditions (Barlos et al, 1986).…”

Section: Structure Determination and Refinementmentioning

confidence: 98%

Crystal structure of N^α-tritylleucyl-(1-benzotriazolyl ester)

Vlassi¹,

Germain²,

Barlos³

et al. 1990

Zeitschrift Für Kristallographie - Crystalline Materials

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The crystal structure of the title compound (C31H30N4O2, M w = 490.61) has been determined by X-ray diffraction methods in order to determine possible intramolecular interactions (Η-bonds) between the Η-atom of the chrial C-atom of amino acids and the N2 atom of the benzotriazolyl group. Crystals are orthorombic, space group / > 2 1 2 1 2 1 with a = 8.836(1), b = 15.471(1), c = 19.809(2) A, V= 2698.5(5) A 3 , Ζ = 4, D = 1.21 gem -3 , λ (CuKoi) = 1.5418 Α, μ = 0.39cm -1 , f(000) = 1040, room temperature. The final R is 0.055 for 2133 observed reflections. The structure determination showed no intramolecular interactions between the Η-atom (H20) of the chiral C-atom (C20) and the N2 atom of the benzotriazolyl group [C20-C25-01 -N2 = 169.63(0.28)].

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Section: Structure Determination and Refinementmentioning

confidence: 98%

Crystal structure of N^α-tritylleucyl-(1-benzotriazolyl ester)

Vlassi¹,

Germain²,

Barlos³

et al. 1990

Zeitschrift Für Kristallographie - Crystalline Materials

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“…Several strategies to suppress or reduce on-resin aggregations have been described and include pseudoprolines, 24 solvent composition, 25 and chaotropic salts, 26,27 however, the utility is limited and the efficiency is variable. Heating has emerged [28][29][30][31][32][33] as an additional parameter in SPPS and is likely to reduce both inter-and intramolecular aggregation, consequently leading to reduced coupling times and improved coupling efficiency of bulky and b-branched amino acids. Is heating above room temperature during the chemical synthesis of peptides a good idea?…”

Section: Introductionmentioning

confidence: 99%

Microwave heating in solid-phase peptide synthesis

et al. 2012

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The highly refined organic chemistry in solid-phase synthesis has made it the method of choice not only to assemble peptides but also small proteins - mainly on a laboratory scale but increasingly also on an industrial scale. While conductive heating occasionally has been applied to peptide synthesis, precise microwave irradiation to heat the reaction mixture during coupling and N(α)-deprotection has become increasingly popular. It has often provided dramatic reductions in synthesis times, accompanied by an increase in the crude peptide purity. Microwave heating has been proven especially relevant for sequences which might form β-sheet type structures and for sterically difficult couplings. The beneficial effect of microwave heating appears so far to be due to the precise nature of this type of heating, rather than a peptide-specific microwave effect. However, microwave heating as such is not a panacea for all difficulties in peptide syntheses and the conditions may need to be adjusted for the incorporation of Cys, His and Asp in peptides, and for the synthesis of, for example, phosphopeptides, glycopeptides, and N-methylated peptides. Here we provide a comprehensive overview of the advances in microwave heating for peptide synthesis, with a focus on systematic studies and general protocols, as well as important applications. The assembly of β-peptides, peptoids and pseudopeptides are also evaluated in this critical review (254 references).

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“…[19] Furthermore, Trt-amino acids, although difficult to couple to the peptide sequence, are practically free of racemization, again due to the steric hindrance induced around the a-H. [20] Moreover, backbone protection, such as the introduction of the 2-hydroxy-4-methoxy benzyl (Hmb) group [21] and the use of pseudoprolines [22] have enabled the synthesis of difficult peptides by disrupting secondary structure formation. Herein, we describe a new concept of protection based on conformational mobility restriction.…”

mentioning

confidence: 99%

Protection by Conformationally Restricted Mobility: First Solid‐Phase Synthesis of Triostin A

Tulla‐Puche¹,

Marcucci²,

Fermin³

et al. 2008

Chemistry A European J

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Conformationally restricted mobility: The application of an efficient solid‐phase strategy based on protection by conformationally restricted mobility (see scheme) has allowed, for the first time, the synthesis and determination of the biological activity of the two triostin A conformers, which result from the isomerization cis/trans of the N‐methyl group of Cys. The most polar conformer showed the greatest inhibitory effect on cell growth.

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Racemisierungsfreie Peptidsynthese bei erhöhter Temperatur

Abstract: N‐Tritylaminosäure‐(1‐benzotriazolylester) 1 werden bei 30–80°C in Gegenwart von überschüssigem Triethylamin racemisierungsfrei an Amino‐Komponenten gekuppelt.

Cited by 34 publications

References 4 publications

Crystal structure of N^α-tritylleucyl-(1-benzotriazolyl ester)

Crystal structure of N^α-tritylleucyl-(1-benzotriazolyl ester)

Microwave heating in solid-phase peptide synthesis

Protection by Conformationally Restricted Mobility: First Solid‐Phase Synthesis of Triostin A

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Racemisierungsfreie Peptidsynthese bei erhöhter Temperatur

Abstract: N‐Tritylaminosäure‐(1‐benzotriazolylester) 1 werden bei 30–80°C in Gegenwart von überschüssigem Triethylamin racemisierungsfrei an Amino‐Komponenten gekuppelt.

Cited by 34 publications

References 4 publications

Crystal structure of Nα-tritylleucyl-(1-benzotriazolyl ester)

Crystal structure of Nα-tritylleucyl-(1-benzotriazolyl ester)

Microwave heating in solid-phase peptide synthesis

Protection by Conformationally Restricted Mobility: First Solid‐Phase Synthesis of Triostin A

Contact Info

Product

Resources

About

Crystal structure of N^α-tritylleucyl-(1-benzotriazolyl ester)

Crystal structure of N^α-tritylleucyl-(1-benzotriazolyl ester)