987-84-8

Basic information

• Product Name: Z-GLU-PHE-OH
• Synonyms: N-CARBOBENZOXY-ALPHA-L-GLUTAMYL-L-PHENYLALANINE;Z-L-ALPHA-GLUTAMYL-L-PHENYLALANINE;Z-L-GLUTAMYL-L-PHENYLALANINE;Z-GLU-PHE-OH;3-phenyl-N-[N-[(phenylmethoxy)carbonyl]-L-alpha-glutamyl]-L-alanine;NSC89650;Z-L-A-GLUTAMYL-L-PHENYLALANINE;Cbz-L-Glu-L-Phe-OH
• CAS NO: 987-84-8
• Molecular Formula: C₂₂H₂₄N₂O₇
• Molecular Weight: 428.44
• EINECS: 213-581-2
• Mol File: 987-84-8.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 760.4 °C at 760 mmHg
• Flash Point: 413.7 °C
• Appearance: /
• Density: 1.325 g/cm³
• Vapor Pressure: 2.62E-24mmHg at 25°C
• Refractive Index: 1.592
• Storage Temp.: -15°C
• CAS DataBase Reference: Z-GLU-PHE-OH(CAS DataBase Reference)
• NIST Chemistry Reference: Z-GLU-PHE-OH(987-84-8)
• EPA Substance Registry System: Z-GLU-PHE-OH(987-84-8)

Safety Data

• Hazardous Substances Data: 987-84-8(Hazardous Substances Data)

Usage

Chemical Properties

White powder

InChI:InChI=1/C22H24N2O7/c25-19(26)12-11-17(24-22(30)31-14-16-9-5-2-6-10-16)20(27)23-18(21(28)29)13-15-7-3-1-4-8-15/h1-10,17-18H,11-14H2,(H,23,27)(H,24,30)(H,25,26)(H,28,29)

Upstream product

• 4124-76-9 N-(benzyloxycarbonyl)-L-glutamic acid anhydride 
• 25126-07-2 N-(benzyloxycarbonyl)-L-glutamic acid, α-phenyl ester 
• 102111-64-8 N-(N-benzyloxycarbonyl-α-L-glutamyl)-D-phenylalanine ethyl ester 
• 16874-17-2 L-phenylalanine tert-butyl ester 
• 3081-24-1 H-Phe-OEt 
• 1155-62-0 N-benzyloxycarbonyl-L-glutamic acid 
• 886981-21-1 benzyl N-[(1S)-1-acetyl-4-(1H-1,2,3-benzotriazol-1-yl)-4-oxobutyl]carbamate 
• 63-91-2 L-phenylalanine 
• 5672-83-3 Z-L-GluOMe 
• 104016-30-0 Z-α-Glu-Phe-O-t-Bu 
• 102111-64-8 N-(N-benzyloxycarbonyl-α-L-glutamyl)-L-phenylalanine ethyl ester 

Downstream Products

• 6398-06-7 N-benzyloxycarbonyl-L-isoglutamine 
• 20556-22-3 N-γ-L-glutamyl-L-phenylalanine 

Relevant articles and documents

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.