Synthesis and β‐conformation of sequential polypeptides containing arginine, histidine, and leucine

Barbier, Bernard; Caille, Anita; Brack, Andrè

doi:10.1002/bip.360231112

Cited by 13 publications

(12 citation statements)

References 25 publications

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“…Samples of alternating poly(Val-Lys) of different chain-length were prepared by polycondensation of the p-nitrophenyl ester of the corresponding protected dipeptide, HCI, H-Val-Lys(Z)-ONp in the presence of one equivalent of 1-hydroxybenzotriazole [20] and of triethylamine. Lysine side-chains were deprotected by HBr in trifluroracetic acid [18].…”

Section: The Stability Is Related To Chain-lengthmentioning

confidence: 99%

Selective emergence and survival of early polypeptides in water

Brack

1987

Origins Life Evol Biosphere

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Oligopeptides essential to primitive cells could not be obtained just by raising the background noise of organic compounds produced by a prebiotic chemistry working at random. Selection pathways were required. Experimental evidence is given for selective condensation of amino acids in water as well as for selective resistance to degradation. It is shown that N-carboxyanhydrides are good candidates for chemical selection in water. They are formed when active esters of amino acids are left in the presence of bicarbonate ions or when N,N'-carbonyldiimidazole is used as condensing agent. Polymerization of a mixture of proteinaceous and non-proteinaceous amino acids leads to an enrichment in the proteinaceous ones plus alpha-aminobutyric acid. Selective resistance toward degradation of beta-pleated sheet conformation is used to exemplify a possible accumulation of homochiral sequences made of hydrophilic and strong hydrophobic residues. Amino acids with branched aliphatic side-chains are selected but those having short linear aliphatic side-chains such as alpha-aminobutyric acid or norvaline are not.

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Section: The Stability Is Related To Chain-lengthmentioning

confidence: 99%

Selective emergence and survival of early polypeptides in water

Brack

1987

Origins Life Evol Biosphere

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“…The final purity was checked by HPLC on a C18 reverse-phase column (Merck). The 2'-deoxyguanosine-3',5'-bisphosphoimidazolide (ImpdGplm) was prepared as described by Schwartz et al (1987) and poly (Leu-Lys) and poly (Arg-Leu) were synthesized according to Brack and CaiUe (1978) and Barbier et al (1984), respectively.…”

Section: Methodsmentioning

confidence: 99%

Polypeptide-assisted oligomerization of analogs in dilute aqueous solution

1993

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Poly (Leu-Lys) was shown to assist the oligomerization of activated nucleotide diphosphates. Short oligomers of pdGp are formed in dilute solution. Activated oligomers can complex to the polypeptide and polymerize to form longer oligomers. Oligomers up to the 18-mer can be obtained under these conditions from 1 x 10 .3 M ImpdGpIm in the absence of a preformed polynucleotide template. The total yield of polymerization remains limited although 50% more pyrophosphate bonds are formed in the presence of polypeptide. However, the elongation effect is more significant since the yield of oligomers longer than the decamer is increased by a factor of 60. The possible prebiotic implications of these experiments are discussed.

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“…(1984). Poly(Arg-Leu) with a number average molecular weight of 4200 and poly(Leu-Arg-Arg-Leu) with a number average molecular weight of 6300 were obtained by condensation of the p-nitrophenyl esters of the corresponding peptides as already described by Barbier et al (1984) and Barbier and Brack (1986). Poly(Glu-Ser-Glu) (Chaves and Trudelle, 1975) was a gift from Dr Y. Trudelle.…”

Section: Methodsmentioning

confidence: 99%

“…Strict alternation of hydrophilic and hydrophobic residues induces a/3-structure formation in water in the presence of salt (Brack and Orgel, 1975;Brack and Caille, 1978;Barbier et al, 1984). With poly(Val-Lys), a bitayer formation with a hydrophobic interior and a positively charged hydrophilic exterior has been described.…”

Section: Introductionmentioning

confidence: 97%

Search for catalytic properties of simple polypeptides

Barbier

Brack

1987

Origins Life Evol Biosphere

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Simple polypeptides were used as possible supports for nucleotide polymerization, in the absence of any preformed polynucleotide template. Sequential copolymers of alanine and glycine, water soluble polypeptides based on arginine and poly(Glu-Ser-Glu) have been tested. No catalytic effect has been found although poly(Glu-Ser-Glu) favors the 2'-5' internucleotide linkage. More interestingly, polypeptides containing arginine residues strongly accelerate the hydrolysis of oligoadenylic acids. The influence of pH, temperature, nature of the buffer and polypeptide sequence was investigated.

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Synthesis and β‐conformation of sequential polypeptides containing arginine, histidine, and leucine

Cited by 13 publications

References 25 publications

Selective emergence and survival of early polypeptides in water

Selective emergence and survival of early polypeptides in water

Polypeptide-assisted oligomerization of analogs in dilute aqueous solution

Search for catalytic properties of simple polypeptides

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