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CA1046441A Expired / Lapsed CA ⏱️ 0.0 years remaining

Peptide synthesis using pepsin

Assignee: Nitto Boseki Co Ltd
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Filing: 1975-04-29
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Granted: 1979-01-16
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Expires: 1995-04-29
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Abstract

Abstract ABSTRACT OF THE DISCLOSURE The present invention provides a process for producing a peptide having the formula X-A-B-C-Y (III) wherein A represents Ala , Gln., Asn., .omega.-BOC-Lys., Leu., Gly., Glu., or Pro; A may be A1 - A2 and A1 represents a hydrophilic amino acid residue and A2 represents Val., Met., Leu. or Gln.; B represents Phe., Tyr., Leu., Met., Glu., Asp., Gln., Asn or Trp.; C represents Phe., Leu., Ileu., Tyr., Cys-SBzl., Ser-OBzl., Trp. or Met.; X represents an .alpha.-amino acid protective group; an amino acid residue having N-terminal protective group or a peptide residue having N-terminal protective group; Y represents a carboxyl protective group; an amino acid residue having C-terminal protective group or a peptide residue having C-terminal protective group, which process comprises reacting a peptide having the formula X-A-B-OH (I) with an amino acid or a peptide having the formula H-C-Y (II) in the presence of enzyme pepsin. The peptides of formula III have physiological activity.

Inventors

  • 👤 Yoshikazu Isowa
  • 👤 Takeshi Nagasawa
  • 👤 Katsumasa Kuroiwa
  • 👤 Koichi Narita

Bibliographic Details

Application Number —
Jurisdiction CA
Data Source google_patents
Last Synchronized 2026-11-09 04:28
CPC Classifications
C; C07; C07K; C07K7/00; C07K7/04; C07K7/22; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/55

Claims Analysis

Total Claims: 10
Claim 1
Independent Claim 178 words
A process for producing a peptide having the formula X-A-B-C-Y (III) wherein A represents Ala., Gln., Asn., .omega.-BOC-Lys., Leu., Gly., Glu., or Pro; A may be A1 - A2 and A1 represents a hydrophilic amino acid residue and A2 represents Val., Met., Leu. or Gln.; B represents Phe., Tyr., Leu., Met., Glu., Asp., Gln., Asn or Trp,; C represents Phe., Leu., Ileu., Tyr., Cys-SBzl., Ser-OBzl., Trp. or Met.; X represents an .alpha.-amino acid protective group; an amino acid residue having N-terminal protective group or a peptide residue having N-terminal protective group; Y represents a carboxyl protective group; an amino acid residue having C-terminal pro-tective group or a peptide residue having C-terminal protective group, which process comprises reacting a peptide having the formula X-A-B-OH (I) with an amino acid or a peptide having the formula H-C-Y (II) in a weight ratio of the compound of formula (II) to the compound of formula (I) from 1 : 5 to 5 : 1 in the presence of enzyme pepsin in an amount from 0.4 to 400 mg. per mole of reactants.
Claim 2
Dependent Claim 178 words
A process for producing a peptide having the formula X-A-B-C-Y (III) wherein A represents Ala., Gln., Asn., .omega.-BOC-Lys., Leu., Gly., Glu., or Pro; A may be A1 - A2 and A1 represents a hydrophilic amino acid residue and A2 represents Val., Met., Leu. or Gln.; B represents Phe., Tyr., Leu., Met., Glu., Asp., Gln., Asn or Trp,; C represents Phe., Leu., Ileu., Tyr., Cys-SBzl., Ser-OBzl., Trp. or Met.; X represents an .alpha.-amino acid protective group; an amino acid residue having N-terminal protective group or a peptide residue having N-terminal protective group; Y represents a carboxyl protective group; an amino acid residue having C-terminal pro-tective group or a peptide residue having C-terminal protective group, which process comprises reacting a peptide having the formula X-A-B-OH (I) with an amino acid or a peptide having the formula H-C-Y (II) in a weight ratio of the compound of formula (II) to the compound of formula (I) from 1 : 5 to 5 : 1 in the presence of enzyme pepsin in an amount from 0.4 to 400 mg. per mole of reactants.
Claim 3
Dependent Claim 40 words
The process according to Claim 1 in which the peptide of formula I has the formula X-A-B-OH wherein A represents Ala., Gln., Asn., .omega.-BOC-Lys., or Gly.; and B represents Phe., Tyr., Leu., or Met.; X is defined in Claim 1.
Claim 4
Dependent Claim 32 words
The process according to Claim 1 in which the peptide of formula I has the formula X-A-B-OH wherein A represents Glu., , Pro.; and B and X are defined in Claim 1.
Claim 5
Dependent Claim 40 words
The process according to Claim 1 in which the peptide of formula I has the formula wherein A1 represents a hydrophilic amino acid residue and A2 represents Val., Met., Leu. or Gln.; B and X are defined in Claim 1.
Claim 6
Dependent Claim 35 words
The process according to Claim 1 in which in the amino acid or a peptide having the formula H-C-Y C represents Phe., Leu., Ileu., Tyr., Cys-SBzl., or Ser-OBzl; and Y is defined in Claim 1.
Claim 7
Dependent Claim 28 words
The process according to Claim 1 wherein the reaction is effected at a temperature from 20 - 50°C in a buffer solution having pH of 2 - 6.
Claim 8
Dependent Claim 27 words
A process according to Claim 6 in which the temperature is from 30°C to 40°C and the pH of the buffer solution is from 3 - 5.
Claim 9
Dependent Claim 23 words
A process as claimed in Claim 6, 7 or 8 in which the reactant is effected in water or a water miscible medium.
Claim 10
Dependent Claim 34 words
A process as claimed in Claim 6, 7 or 8 in which the ratio of the compound of formula (II) to the compound of formula (I) is 1 : 2 to 2 : 1.

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