The Application of p-Nitrobenzyl Chloroformate to Peptide Synthesis

Carpenter, Frederick H.; Gish, Duane T.

doi:10.1021/ja01135a030

Cited by 73 publications

(18 citation statements)

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“…(1 l). -This compound was prepared according to a previously described procedure,' (12).-A solution of Z 2 0 (12 g, 42 mmol) in dry CH,Cl, (15 ml) was added dropwise to a cooled solution of compound (11) (3.0 g, 19 mmol) in dry CH,Cl, (15 ml), and the resulting mixture was stirred for 3 h. The solvent was removed under reduced pressure and the colourless residue was chromatographed on silica (CH,Cl,-Me,CO, 4: 1) to afford chromatographically essentially pure (G) product (12) as a pale yellow oil (6.1 g, 76%); 6, 7.34 (s, 10 H, ArH), 5.12 and 5.08 (2 s, 4 H, CH2Ph), 4.14 (s, 2 H, NCH,N), 3.53 (t, 2 H) and 3.13-3.23 (m, 2 H) (CH,NZ), 2.71 (t, 2 H), and 2.29-2.53 (m, 2 H) (CH,N), and 1.33-1.74 (m, 6 H, CCH,C); 6, 156.4 and 155.0 (CO), 136.6, 128.4, and 128.0 (Arc), 67.0 and 66.4 (CH2Ph),65.0(NCH,N), 52.4 and 52.2 (2 x NCH,),43.8 and 40.8 (2 x ZNCH,C), and 27.6, 24.4, and 22.9 (CCH,C). (13).-To a stirred solution of compound (12) (4.4 g, 10 mmol) in dry MeCN (20 ml) was added DMAP (128 mg, 1.03 mmol), followed by Boc,O (2.5 g, 11 mmol).…”

Section: N'n4-methyfenespermidinementioning

confidence: 99%

Selective protection of polyamines: synthesis of model compounds and spermidine derivatives

Almeida¹,

Grehn²,

Ragnarsson³

1988

J. Chem. Soc., Perkin Trans. 1

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Section: N'n4-methyfenespermidinementioning

confidence: 99%

Selective protection of polyamines: synthesis of model compounds and spermidine derivatives

Almeida¹,

Grehn²,

Ragnarsson³

1988

J. Chem. Soc., Perkin Trans. 1

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“…Glycyl-6-aminopenicillanic acid (Gly-6-APA) N-(4-Nitrobenzyloxycarbonyl)glycine was prepared by allowing glycine (Janssen, Beerse, Belgium) to react with 4-nitrobenzylchloroformate (Fluka, Buchs, Switzerland) as described by Carpenter and Gish (1952). The product was subsequently coupled to 6-APA as described by Doyle et al (1962).…”

Section: Synthesesmentioning

confidence: 99%

Synthesis, purification and kinetic properties of fluorescein-labelled penicillins

Lakaye

Damblon

Jamin

et al. 1994

Biochemical Journal

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The synthesis and properties of six fluorescein-labelled penicillins are reported. The two isomers of fluoresceyl-glycyl-6-amino-penicillanic acid are probably the best compounds to use for detection of all the penicillin-binding proteins (PBPs) present in a bacterial membrane preparation. However, the derivatives of ampicillin were much more efficient against Enterobacter aerogenes PBP3. The two isomers obtained when a commercial mixture of the two isomers of carboxyfluorescein was used most often exhibited similar properties, but the Streptomyces R61 extracellular DD-peptidase was only efficiently acylated by the 5'-carboxyfluorescein derivative of glycyl-6-aminopenicillanic acid.

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“…Although thep-nitrobenzyloxycarbonyl group is more acid resistant than the Z group the protected methionine residue and its active ester tended to decompose (cf. Carpenter & Gish, 1952). The use of the 2,4dinitrophenyl derivative of methionine seemed attractive, as it alloWs simple determination of the extent of insulin protection by measurement of the characteristic absorption at 350nm.…”

Section: Characterization Ofinsulin Derivativesmentioning

confidence: 99%

Semisynthetic analogues of insulin. The use of N-substituted derivatives of methionine as acid-stable protecting groups

Saunders

Offord

1977

Biochemical Journal

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1. We describe the use of benzyloxycarbonylmethionine and ethoxycarbonylmethionine for the selective protection of the amino groups of glycine-A1 and lysine-B29 of pig insulin. We have used the Edman method to remove residues from the N-terminal and of the B-chain of the N(A1)N(B29)-di-protected derivatives. The benzyloxycarbonyl group shows slight but noticeable lability in the acid-cleavage step, but the ethoxycarbonyl group remained intact even after five cycles of degradation. 2. We have prepared the following truncated forms of insulin via the di(ethoxycarbonylmethionyl) derivative: des-Phe(B1)-insulin;des-(Phe(B1)-Val(B2))-insulin; des-(Phe(B1)-Val(B2)-Asn(B3))-insulin;des- (Phe(B1)-Val(B2)-Asn(B3)-Gln(B4))-insulin; des-(Phe(B1)-Val(B2)-Asn(B3) -Gln(B4)-His(B5))-insulin. 3. Insulin was re-synthesized from the di-protected des-Phe(B1)-insulin by reaction with an active ester of t-butoxycarbonyl-l-phenylalanine. The product after deprotection crystallized, and the immunoreactivity of the crystalline material was identical with that of the native protein. 4. We have prepared the following analogues of insulin in a similar manner: [l-Ala(B1)]insulin; [l-Val(B1)]insulin; [l-Tyr(B1)]insulin; [m-F-l-Phe(B1)]insulin; [o-F-l-Phe(B1)]-insulin; [o-F-l-Phe(B2)]des-Phe(B1)-insulin. All had between 34 and 62% of the activity of insulin in the fat-cell test. 5. We have also investigated the use of the benzyol, toluene-p-sulphonyl, p-nitrobenzyloxycarbonyl and 2,4-dinitrophenyl groups for the N-protection of the methionine active esters. Each should have had some particular advantage over the benzyloxycarbonyl and ethoxycarbonyl groups, but all proved in practice to have disadvantages that more than outweighed anything in their favour.

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The Application of p-Nitrobenzyl Chloroformate to Peptide Synthesis

Cited by 73 publications

References 0 publications

Selective protection of polyamines: synthesis of model compounds and spermidine derivatives

Selective protection of polyamines: synthesis of model compounds and spermidine derivatives

Synthesis, purification and kinetic properties of fluorescein-labelled penicillins

Semisynthetic analogues of insulin. The use of N-substituted derivatives of methionine as acid-stable protecting groups

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