57850-17-6

Basic information

• Product Name: Z-TRP-TRP-OH
• Synonyms: Z-TRP-TRP-OH;Z-Trp-Trp-OH≥ 98% (HPLC)
• CAS NO: 57850-17-6
• Molecular Formula: C₃₀H₂₈N₄O₅
• Molecular Weight: 524.57
• Mol File: 57850-17-6.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• Refractive Index: 1.702
• Storage Temp.: -15°C
• CAS DataBase Reference: Z-TRP-TRP-OH(CAS DataBase Reference)
• NIST Chemistry Reference: Z-TRP-TRP-OH(57850-17-6)
• EPA Substance Registry System: Z-TRP-TRP-OH(57850-17-6)

Safety Data

• Hazardous Substances Data: 57850-17-6(Hazardous Substances Data)

Usage

Chemical Properties

White to off-white powder

InChI:InChI=1/C30H28N4O5/c35-28(33-27(29(36)37)15-21-17-32-25-13-7-5-11-23(21)25)26(14-20-16-31-24-12-6-4-10-22(20)24)34-30(38)39-18-19-8-2-1-3-9-19/h1-13,16-17,26-27,31-32H,14-15,18H2,(H,33,35)(H,34,38)(H,36,37)

Upstream product

• 73-22-3 L-Tryptophan 
• 64693-64-7 N^α-benzyloxycarbonyl-L-tryptophyl chloride 
• 4299-70-1 L-tryptophan methyl ester 
• 7432-21-5 N-carbobenzyloxy-L-tryptophane 
• 850232-59-6 benzyl N-[(1S)-2-(1H-1,2,3-benzotriazol-1-yl)-1-(1H-indol-3-ylmethyl)-2-oxoethyl]carbamate 
• 17689-58-6 N-(benzyloxycarbonyl)-L-tryptophanyl-L-tryptophan methyl ester 

Downstream Products

• 925913-34-4 Cbz-Trp-Trp-Phe-N-methyl-O-methylhydroxylamine 
• 1057092-58-6 C₄₂H₄₀N₈O₆ 
• 119645-70-4 1-[(S)-1-Benzyloxycarbonylamino-2-(1H-indol-3-yl)-ethyl]-4,9-dihydro-3H-β-carboline-3-carboxylic acid 
• 886981-42-6 benzyl N-{(S)-1-[(S)-2-benzotriazol-1-yl-1-(1H-indol-3-ylmethyl)-2-oxoethylcarbamoyl]-2-(1H-indol-3-yl)ethyl}carbamate 
• 82989-13-7 Z-(L)-Trp-(L)-Trp-(L)-Pro-PNP 

Relevant articles and documents

Convenient synthesis of C-terminal di- and tri-peptide amides from N-protected dipeptidoylbenzotriazoles

N-Protected dipeptidoylbenzotriazoles react with aqueous ammonia to give dipeptide primary amides (77-98%) and with N-unprotected α-amino amides to afford tripeptide primary amides (82-86%).

The efficient preparation of di- and tripeptides by coupling N-(Cbz- or Fmoc-α-aminoacyl)benzotriazoles with unprotected amino acids

N-(Cbz- or Fmoc-α-aminoacyl)benzotriazoles 2 and N-protected peptidoylbenzotriazoles 6 are coupled in aqueous acetonitrile solution with free amino acids or dipeptides to prepare: (i) 22 chirally pure dipeptides 5a-v (in an average yield of 82%) from N-(Cbz- or Fmoc-α-aminoacyl)benzotriazoles 2 and unprotected amino acids, (ii) five chiral tripeptides 7a-e (in an average yield of 75%) from N-protected peptidoylbenzotriazoles 6 and unprotected amino acids, (iii) one chiral tripeptide 7g (62%) from N-(Cbz- or Fmoc-α- aminoacyl)benzotriazole 2a and the free dipeptide 8. In all, N-(Cbz- or Fmoc-α-aminoacyl)benzotriazole derivatives of 17 of the 20 naturally occurring amino acids were used, including those containing the following unprotected side chain functionalities: alcoholic -OH (Ser), indole -NH (Trp), imidazole -NH, phenolic -OH (Tyr), -CONH2 (Gln, Asn), -SH (Cys), -CO2H (Glu, Asp), and -S-S (Cystine). Support for the complete retention of chirality was obtained by parallel experiments involving D-Ala, L-Ala, and DL-Ala for the preparation of di- and tripeptides. This and other evidence for chiral integrity was supported by NMR and HPLC analyses. Georg Thieme Verlag Stuttgart.

Peptide Synthesis Using Unprotected Amino Acids and Novel Imidoyl Halide Reagents

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