Synthese einer geschützten Heptapeptidsequenz aus dem Tyrocidin B

Zahn, Helmut; Brandenburg, Dietrich

doi:10.1002/jlac.19666920125

Cited by 14 publications

(1 citation statement)

References 41 publications

(2 reference statements)

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“…Peptide 17 was obtained from 5a (10 mmol) and HCl.H-Tyr(OBzl)-Phe-OBzl [19] (10 mmol) as described for 13. Yield 0.6 g (80%); mp 100 °C; homogeneous (…”

Section: Boc-ala(thz)-tyr(bzl)-phe-obzl (16)mentioning

confidence: 99%

Synthesis and Antimicrobial Activity in Vitro of New Amino Acids and Peptides Containing Thiazole and Oxazole Moieties

Stanchev¹,

Tabakova²,

Videnov³

et al. 1999

Arch. Pharm. Pharm. Med. Chem.

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“…Peptide 17 was obtained from 5a (10 mmol) and HCl.H-Tyr(OBzl)-Phe-OBzl [19] (10 mmol) as described for 13. Yield 0.6 g (80%); mp 100 °C; homogeneous (…”

Section: Boc-ala(thz)-tyr(bzl)-phe-obzl (16)mentioning

confidence: 99%

Synthesis and Antimicrobial Activity in Vitro of New Amino Acids and Peptides Containing Thiazole and Oxazole Moieties

Stanchev¹,

Tabakova²,

Videnov³

et al. 1999

Arch. Pharm. Pharm. Med. Chem.

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2‐Benzoyl‐2‐ethoxycarbonylvinyl‐1 and 2‐benzoylamino‐2‐methoxy‐carbonylvinyl‐1 as N‐protecting groups in peptide synthesis. Their application in the synthesis of dehydropeptide derivatives containing N‐terminal 3‐heteroarylamino‐2,3‐dehydroalanine

Svete¹,

Aljaz‐Rozic²,

Stanovnik³

1997

Journal of Heterocyclic Chem

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Ethyl 2‐benzoyl‐3‐dimethylaminopropenoate (6) and methyl 2‐benzoylamino‐3‐dimethylaminopropenoate (46) were used as reagents for the protection of the amino group with 2‐benzoyl‐2‐ethoxycarbonylvinyl‐1 and 2‐benzoylamino‐2‐methoxycarbonylvinyl groups in the peptide synthesis. Reactions of ethyl 2‐benzoyl‐3‐dimethylaminopropenoate (6) with α‐amino acids gave N‐(2‐benzoyl‐2‐ethoxycarbonylvinyl‐1)‐α‐amino acids 13–19. These were coupled with various amino acid esters to form N‐(2‐benzoyl‐2‐ethoxycar‐bonylvinyl‐1)‐protected dipeptide esters 20–31. The removal of 2‐benzoyl‐2‐ethoxycarbonylvinyl‐1 group, which was achieved by hydrazine monohydrochloride or hydroxylamine hydrochloride, afforded hydrochlo‐rides of dipeptide esters 32–41 in high yields. Similarly, the substitution of the dimethylamino group in methyl 2‐benzoylamino‐3‐dimethylaminopropenoate (46) by glycine gave N‐(2‐benzoylamino‐2‐methoxycar‐bonylvinyl‐1)glycine (47), which was coupled with glycine ethyl ester to give N‐[N‐(2‐benzoylamino‐2‐methoxycarbonylvinyl‐1)glycyl]glycine ethyl ester (48). Treatment of 48 with 2‐arnino‐4,6‐dirnethylpyrimi‐dine afforded N‐[glycyl]glycine ethyl ester hydrochloride (34) in high yield. Amino acid esters and dipeptide esters were employed in the preparation of tri‐ 58‐70, tetra‐ 71–82, and pentapeptide esters 83–85 containing N‐terminal 3‐heteroarylamino‐2,3‐dehydroalanine. 2‐Chloro‐4,6‐dimethoxy‐1,3,5‐triazine was employed as a coupling reagent for the preparation of peptides 58–85.

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On the repetitive excess mixed anhydride method for the synthesis of peptides. Synthesis of the sequence 1‐10 of human growth hormone

Beyerman¹,

Leer²,

Floor³

1973

Recl. Trav. Chim. Pays‐Bas

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The synthesis of the fully protected N‐terminal decapeptide of human growth hormone, Boc‐Phe‐Pro‐Thr(Bzl)‐Ile‐Pro‐Leu‐Ser(Bzl)‐Arg(NO2)‐Leu‐Phe‐OMe (HGH 1‐10) by the repetitive excess mixed anhydride (REMA) method is described. Starting from Phe‐OMe this sequence was synthesized in a stepwise manner in an overall yield of 59%. In the coupling of Boc‐Ile to Pro‐Leu‐Ser(Bzl)‐Arg‐(NO2)‐Leu‐Phe‐OMe the isobutoxycarbonyl derivative of the amino‐component was isolated. This problem of reaction on the undesirable side of the mixed anhydride in the couplings to proline‐peptides was circumvented by the coupling of dipeptides, viz. Boc‐Ile‐Pro and Boc‐Phe‐Pro. Also a larger peptide fragment, ZPhe‐Pro‐Thr‐Ile‐Pro (HGH 1‐5), was conveniently coupled to the C‐terminal pentapeptide. Synthesis of Boc‐Leu‐Ser(Bzl)‐Arg(NO2)‐Leu‐Phe‐OMe (HGH 6‐10) was performed with and without intermediate purification. It was found that the yield was higher when no purifications were applied. HGH 6‐10 was compared with the corresponding peptide synthesized by the solid phase method. Both products were found to be identical with regard to melting point, optical rotation and chromatographic behaviour. The decapeptide, on deprotection, showed identical chromatographic behaviour with a product obtained by the solid phase method. The optical rotations showed a small difference; no significant racemization could be detected on digestion with L‐amino‐acid oxidase.

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Synthese einer geschützten Heptapeptidsequenz aus dem Tyrocidin B

Cited by 14 publications

References 41 publications

Synthesis and Antimicrobial Activity in Vitro of New Amino Acids and Peptides Containing Thiazole and Oxazole Moieties

Synthesis and Antimicrobial Activity in Vitro of New Amino Acids and Peptides Containing Thiazole and Oxazole Moieties

2‐Benzoyl‐2‐ethoxycarbonylvinyl‐1 and 2‐benzoylamino‐2‐methoxy‐carbonylvinyl‐1 as N‐protecting groups in peptide synthesis. Their application in the synthesis of dehydropeptide derivatives containing N‐terminal 3‐heteroarylamino‐2,3‐dehydroalanine

On the repetitive excess mixed anhydride method for the synthesis of peptides. Synthesis of the sequence 1‐10 of human growth hormone

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