Synthese von Polypeptiden XXII. Derivate des l‐Phenylalanin

Fischer, Emil; Schoeller, W. R.

doi:10.1002/jlac.19073570102

Cited by 55 publications

(5 citation statements)

References 4 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Scalemic α-chloro and α-bromo acids are readily prepared from their corresponding α-amino acids, with retention of configuration . Thus, the α-chloro compounds 1a − 3a , and the α-bromo compounds 1b − 3b , were synthesized from l -phenylalanine, l -valine, and l -leucine, respectively.…”

Section: Resultsmentioning

confidence: 99%

“…In this report we describe the regiochemical and stereochemical influence of the α-chloro and α-bromo substituents in the preparation of bromo-substituted optically pure α-chloro and α-bromo carboxylic acid derivatives. Apart from substitution of the α-amino group of suitable proteinogenic α-amino acids there is a lack of methods for the synthesis of optically pure α-chloro and α-bromo acids. Introduction of a versatile bromide functionality to readily available scalemic α-chloro and α-bromo acids would facilitate the preparation of a wider range through structural elaboration.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Selective Bromination of α-Chloro and α-Bromo Carboxylic Acid Derivatives

Shaw

Tan

1996

J. Org. Chem.

View full text Add to dashboard Cite

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Selective Bromination of α-Chloro and α-Bromo Carboxylic Acid Derivatives

Shaw

Tan

1996

J. Org. Chem.

View full text Add to dashboard Cite

“…Related to these peptidylsulphonium salts is the synthesis of a peptide in which the sulphonium group occupies the position of the Lz-amino group, that is, L-C6H5CH2CHS+(CH3)2CO-Ala-Ala-OCH3 (compound 1, Scheme 1). D-Phenylalanine was converted with retention of configuration (Fischer & Schoeller, 1907) to the D-bromo compound 2, Scheme 1) with HBr/NaNO2, and this was elongated with Ala-Ala-OMe by the standard mixed-anhydride procedure. Treatment with NaSCH3 yielded, under inversion, the L-methylthio compound (4, Scheme 1), which was then converted with AgBF4 (Beak & Sullivan, 1982) into the sulphonium salt (1, Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

The inactivation of the cysteinyl exopeptidases cathepsin H and C by affinity-labelling reagents

Angliker

Wikström

Kirschke

et al. 1989

Biochemical Journal

View full text Add to dashboard Cite

An attempt has been made to extend to the cysteinyl exopeptidases cathepsins H and C affinity-labelling approaches shown to be effective with cysteinyl endopeptidases such as cathepsins B and L and the calcium-activated proteinase. This involved the preparation of amino acid and dipeptide derivatives with unblocked N-termini to satisfy the aminopeptidase and dipeptidyl aminopeptidase characteristics of cathepsins H and C respectively. For covalent reactivity, the possibilities examined included diazomethanes (-CHN2), fluoromethanes (-CH2F) and dimethylsulphonium salt [-CH2S+(CH3)2]. A dipeptidylfluoromethane with a free amino group could not be prepared, perhaps due to inherent instability. Cathepsin H was inactivated by 1 microM-H2N-Phe-CH2F (the 'H2N' indicates a free unblocked amino group) (k2 = 1878 M-1.s-1); this reagent was without effect on cathepsins C and B, even at 100-fold this concentration. Analogous selectivity was shown by H2N-Ser(OBzl)-CHN2 and H2N-Phe-CH2S+(CH3)2, members of other classes of covalently binding reagents. For cathepsin C the dipeptide derivatives H2N-Gly-Phe-CHN2 and H2N-Phe-Ala-CH2S+(CH3)2 caused rapid inactivation near 10(-7) M. Higher concentrations inactivated cathepsins H and B, but the rates were slower by two to three orders of magnitude than for cathepsin C.

show abstract

“…JV-Cinnamoyl-L-phenylalanine (22). A mixture of 0.97 g (3.0 mmol) of JV-cinnamoyl-L-phenylalanine ethyl ester (21) in 10 mL of an ethanolic solution of 1 N NaOH was stirred at room temperature overnight.…”

Section: Chci3)mentioning

confidence: 99%

Antineoplastic agents. 1. N-Protected vinyl, 1,2-dihaloethyl, and cyanomethyl esters of phenylalanine

Loeffler¹,

Sajadi²,

Hall³

1977

J. Med. Chem.

View full text Add to dashboard Cite

A series of N-protected vinyl, 1,2-dihaloethyl, and cyanomethyl esters of phenylalanine was synthesized and these compounds were evaluated for antitumor activity against the growth of Ehrlich ascites carcinoma in CF1 male mice (33 mg/kg/day), Walker 256 carcinosarcoma in Sprague-Dawley male rats (2.5 mg/kg/day), and P388 lymphocytic leukemia in DBA/2 mice (20 mg/kg/day). Structure-activity relationships were evaluated and acute toxicity studies (LD50 determinations) in male CF1 mice were also carried out on selected compounds. Carbobenzoxy-L0phenylalanine vinyl ester (5), N-carbobenzoxy-L-phenylalanine 1,2-dibromoethyl ester (12), and N-carbobenzoxy-L-phenylalanine cyanomethyl ester (8) were found to be very potent inhibitors of Ehrlich ascites tumor growth at nontoxic doses cited above. Compounds 5 and 12 also tripled survival time in the Walker 256 system. LD50 values for compounds 5, 12, and 8 were greater than 2000 mg/kg (greater than 6.15 mmol/kg), 74 mg/kg (0.15 mmol/kg), and 150 mg/kg (0.44 mmol/kg), respectively.

show abstract

Synthese von Polypeptiden XXII. Derivate des l‐Phenylalanin

Cited by 55 publications

References 4 publications

Selective Bromination of α-Chloro and α-Bromo Carboxylic Acid Derivatives

Selective Bromination of α-Chloro and α-Bromo Carboxylic Acid Derivatives

The inactivation of the cysteinyl exopeptidases cathepsin H and C by affinity-labelling reagents

Antineoplastic agents. 1. N-Protected vinyl, 1,2-dihaloethyl, and cyanomethyl esters of phenylalanine

Contact Info

Product

Resources

About