Polymerization of amino acids or peptides with diphenyl phosphoryl azide (DPPA)

Nishi, Norio; Nakajima, Bun-ichiro; Hasebe, Nobuyuki; Noguchi, Junzo

doi:10.1016/0141-8130(80)90012-4

Cited by 32 publications

(7 citation statements)

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“…On the other hand, the polymerization of L-histidine containing hexa-or nona-peptide gave a sequential polypeptide having a much greater molecular weight in good yield. 2 The peptide or polypeptide of repeating -AlaGly-sequence is known to be sparingly soluble in various organic solvents. The biggest factor which limits the proceeding of the polymerization might be the solubility of the elongating polypeptide chain in the case of the polymerization of the peptide with -Ala-Gly-sequence.…”

Section: Comparison Of H-ala-gly-oh Polymerizations With Those Of Lonmentioning

confidence: 99%

“…Poly(amino acid)s such as poly(glycine), poly(Lalanine), poly(L-leucine), poly(y-benzyl L-glutamate), poly(e-benzyloxycarbonyl-L-lysine), poly(f3-alanine) and poly(6-aminohexanoic acid) were prepared by this method. 2 Sequential polypeptides such as poly(L-alanylglycine), poly(L-alanylglycyl-Lalanylglycyl-L-alanylglycyl-L-serylglycine ), poly( 0-benzyl-L-seryl-[3-alanylglycyl-L-histidyl-[3-alanylglycine), and poly(f3-benzyl-L-aspartyl-f3-alanylglycyl-O-benzyl-L-seryl-f3-alanylglycyl-L-histidyl-f3-alanylglycine) were also synthesized successfully, as previously reported. 2 In particular, the polymerization of L-histidine-containing hexa-or nonapeptide gave a high-molecular-weight sequential polypeptide.…”

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confidence: 99%

“…2 Sequential polypeptides such as poly( -alanylglycyl-L-histidyl-[3-alanylglycine), and poly(f3-benzyl-L-aspartyl-f3-alanylglycyl-O-benzyl-L-seryl-f3-alanylglycyl-L-histidyl-f3-alanylglycine) were also synthesized successfully, as previously reported. 2 In particular, the polymerization of L-histidine-containing hexa-or nonapeptide gave a high-molecular-weight sequential polypeptide. Thus the DPPA method seems to have the possibility of becoming one of the very convenient and efficient methods for polypeptide synthesis, especially for the synthesis of sequential polypeptides, if the further exhaustive investigation is performed.…”

mentioning

confidence: 99%

“…2 A polypeptide can easily be prepared by just stirring the solution or suspension of amino acid or peptide in a suitable solvent with DPPA and a tertiary amine such as triethylamine. Poly(amino acid)s such as poly(glycine), poly(Lalanine), poly(L-leucine), poly(y-benzyl L-glutamate), poly(e-benzyloxycarbonyl-L-lysine), poly(f3-alanine) and poly(6-aminohexanoic acid) were prepared by this method.…”

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Polymerization of L-Alanylglycine with Diphenylphosphoryl Azide

Nakajima

Nishi

1981

Polym J

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ABSTRACT:The polymerization reactions of L-alanylglycine with diphenylphosphoryl azide (DPPA) were investigated under various reaction conditions. Dimethyl sulfoxide and triethylamine were found to be the most suitable solvent and base, respectively, for this polymerization reaction. A reaction time of two days at room temperature, employing 1.3 equivalent moles of DPPA and 2.6 equivalent moles of triethylamine corresponding to the amount of L-alanylglycine were considered to be the most appropriate reaction condition. In this case, poly(L-alanylglycine) which has the intrinsic viscosity of 0.16 in dichloroacetic acid at 25°C was obtained in 43% yield. Its infrared absorption spectrum and elemental analysis, and the amino acid analysis or the optical rotation for the acid hydrolysate indicated the high purity of poly(L-alanylglycine) obtained by this DPPA method.KEY WORDSDiphenylphosphoryl azide (DPPA) has been used as a convenient reagent for racemization-free peptide synthesis since it was synthesized by Shioiri eta!. in 1972. 1 It is non-explosive and stable enough to be stored for a long time without decomposition.Recently, we reported that this reagent can also be used successfully for the polymerization of amino acids or peptides. 2 A polypeptide can easily be prepared by just stirring the solution or suspension of amino acid or peptide in a suitable solvent with DPPA and a tertiary amine such as triethylamine. Poly(amino acid)s such as poly(glycine), poly(Lalanine), poly(L-leucine), poly(y-benzyl L-glutamate), poly(e-benzyloxycarbonyl-L-lysine), poly(f3-alanine) and poly(6-aminohexanoic acid) were prepared by this method. 2 Sequential polypeptides such as poly( -alanylglycyl-L-histidyl-[3-alanylglycine), and poly(f3-benzyl-L-aspartyl-f3-alanylglycyl-O-benzyl-L-seryl-f3-alanylglycyl-L-histidyl-f3-alanylglycine) were also synthesized successfully, as previously reported. 2 In particular, the polymerization of L-histidine-containing hexa-or nonapeptide gave a high-molecular-weight sequential polypeptide. Thus the DPPA method seems to have the possibility of becoming one of the very convenient and efficient methods for polypeptide synthesis, especially for the synthesis of sequential polypeptides, if the further exhaustive investigation is performed. In developing this method of polymerization, it would be very helpful to investigate in detail the relationship between the reaction conditions and results, using one kind of peptide as a representative.In the present study, the polymerization of Lalanylglycine was investigated in detail to find the most suitable reaction conditions for this peptide and, as a result, useful information by which this DPPA method could be used for the general synthesis of sequential polypeptides was obtained. The detailed s!udy on the composition or the purity of resultant poly(L-alanylglycine) are also reported. EXPERIMENTAL MeasurementsElemental analyses were carried out with a Yanagimoto CHN Corder, Model MT-2. Optical rotations were measured with a Yanagimoto 183

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Section: Comparison Of H-ala-gly-oh Polymerizations With Those Of Lonmentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

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Polymerization of L-Alanylglycine with Diphenylphosphoryl Azide

Nakajima

Nishi

1981

Polym J

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“…The purity of the peptides were confirmed by thin layer chromatography and elemental analysis. Polymerisation of monomer peptide was carried out with diphenylphosphorylazide, as we have described elsewhere (Nishi et al, 1980). The removal of the side-chain protecting groups from the resulting sequential polypeptides was carried out with a methansulphonic acidanisole mixture for the initial polypeptide and with a trifluoromethanesulphonic acid-thioanisole-trifluoroacetic acid mixture for the latter polypeptide.…”

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The inhibition of murine lung metastasis by synthetic polypeptides [poly(arg-gly-asp) and poly(tyr-ile-gly-ser-arg)] with a core sequence of cell adhesion molecules

Saiki

Murata²,

Iida³

et al. 1989

Br J Cancer

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Structure determination and synthesis of lysine isopeptides influencing on cell proliferation

et al. 1997

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The clavicepamines are lysine‐rich basic proteins isolated from saprophytic culture of ergot (Claviceps purpurea), having human pharmacological importance. Based on structure determinations, it was demonstrated that the ϵ‐lysine (poly)peptides are the fundamental structural units of clavicepamines. To study the relationship between chemical structure and biological effect, solution and solid‐phase synthesis of lysine isopeptides were performed. Poly‐ϵ‐lysines were synthesized with polycondensation via application of p‐nitrophenylester temporarily protecting groups together with simultaneous activation. The biological investigations of poly‐ϵ‐lysines showed a cell‐proliferation retarding effect, so they inhibit growth of some animal tumors, practically without toxic side effects. © 1997 John Wiley & Sons, Inc. Biopoly 42: 305–318, 1997

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Polymerization of amino acids or peptides with diphenyl phosphoryl azide (DPPA)

Cited by 32 publications

References 4 publications

Polymerization of L-Alanylglycine with Diphenylphosphoryl Azide

Polymerization of L-Alanylglycine with Diphenylphosphoryl Azide

The inhibition of murine lung metastasis by synthetic polypeptides [poly(arg-gly-asp) and poly(tyr-ile-gly-ser-arg)] with a core sequence of cell adhesion molecules

Structure determination and synthesis of lysine isopeptides influencing on cell proliferation

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