Human chorionic gonadotropin. III. Synthesis of a dotriacontapeptide corresponding to the C-terminal sequence 116-147 of the .BETA.-subunit of human chorionic gonadotropin (hCG).

Kawasaki, Koichi; Kawasaki, Chiye; Tsuda, Yuko; Yagyu, Masami; Okada, Yoshio; Yamaji, Kenji; Такаги, Таичиро; Takahashi, Osamu

doi:10.1248/cpb.28.2699

Cited by 2 publications

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“…Previous preparations of proline peptides by coupling at the proline NH were achieved via carbodiimide methods ,, (i − iii) and active ester methods ,, (iv − vi) (Scheme ). Our method synthesizes proline peptides in short reaction times utilizing mild reaction conditions.…”

Section: Resultsmentioning

confidence: 99%

“…The enantiopurity of dipeptides 10a-d was confirmed by HPLC analyses using Chirobiotic T column (detection at 254 nm, flow rate 0.5 mL/min, and MeOH as solvent): dipeptides 10a,d each gave a single retention time, whereas the diastereomeric mixture (10a + 10a′) showed two retention times as expected (Table 6). Previous preparations of proline peptides by coupling at the proline NH were achieved via carbodiimide methods 47,50,51 (i-iii) and active ester methods 47,52,53 (iv-vi) (Scheme 12). Our method synthesizes proline peptides in short reaction times utilizing mild reaction conditions.…”

Section: Preparation Of Proline-containing Dipeptides (A)mentioning

confidence: 99%

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Efficient Peptide Coupling Involving Sterically Hindered Amino Acids

et al. 2007

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Hindered amino acids have been introduced into peptide chains by coupling N-(Cbz- and Fmoc-alpha-aminoacyl)benzotriazoles with amino acids, wherein at least one of the components was sterically hindered, to provide compounds 3a-e, (3c +3 c'), 5a-d, (5a + 5a'), 6a-c, (6b + 6b'), 8a-c, 9a-e, 10a-d, and (10a + 10a') in isolated yields of 41-95% with complete retention of chirality as evidenced by NMR and HPLC analysis. The benzotriazole activation methodology is a new route for the synthesis of sterically hindered peptides. (Note: compound numbers written within brackets represent diastereomeric mixtures or racemates; compound numbers without brackets represent enantiomers.).

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Section: Resultsmentioning

confidence: 99%

Section: Preparation Of Proline-containing Dipeptides (A)mentioning

confidence: 99%

Efficient Peptide Coupling Involving Sterically Hindered Amino Acids

et al. 2007

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Synthesis of a tetratriacontapeptide corresponding to sequence 112-145 of the β-subunit of hCG and production of antiserum against this synthetic peptide

Yamaji¹,

Такаги

Sugita

et al. 2010

Asia-Oceania Journal of Obstetrics and Gynaecology

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A tetratriacontapeptide(P-34) corresponding to sequence 1 1 2-145 of the @-subunit of hCG(hCG-@) was synthesized by the fragment condensation method.The immunogen was prepared by coupling P-34 to bovine serum albumin by the carbodiimide or glutaraldehyde method.Antiserum was produced by injecting the immunogen into rabbits at multiple intradermal and intrasplenal sites with Freund's complete adjuvant.Eight weeks after the first immunization, antiserum was obtained that bound 30% of 12'I-hCG or 12'I-hCG-@ at a dilution of 1 : 1,000. This binding was inhibited dose-dependently by hCG. In this radioimmunoassay system, the minimal detectable dose of hCG was 500 mIU/ml and, as expected theoretically, no binding to 12'I-hCGa or 12' I-hLH was observed.

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Human chorionic gonadotropin. III. Synthesis of a dotriacontapeptide corresponding to the C-terminal sequence 116-147 of the .BETA.-subunit of human chorionic gonadotropin (hCG).

Cited by 2 publications

References 0 publications

Efficient Peptide Coupling Involving Sterically Hindered Amino Acids

Efficient Peptide Coupling Involving Sterically Hindered Amino Acids

Synthesis of a tetratriacontapeptide corresponding to sequence 112-145 of the β-subunit of hCG and production of antiserum against this synthetic peptide

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