1423324-26-8

Basic information

• Product Name: (S)-methyl 2-((S)-2-((tert-butoxycarbonyl)-amino)-5-methoxy-5-oxopentanamido)pent-4-ynoate
• Synonyms: (S)-methyl 2-((S)-2-((tert-butoxycarbonyl)-amino)-5-methoxy-5-oxopentanamido)pent-4-ynoate
• CAS NO: 1423324-26-8
• Molecular Weight: 647.648
• Mol File: 1423324-26-8.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (S)-methyl 2-((S)-2-((tert-butoxycarbonyl)-amino)-5-methoxy-5-oxopentanamido)pent-4-ynoate(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-methyl 2-((S)-2-((tert-butoxycarbonyl)-amino)-5-methoxy-5-oxopentanamido)pent-4-ynoate(1423324-26-8)
• EPA Substance Registry System: (S)-methyl 2-((S)-2-((tert-butoxycarbonyl)-amino)-5-methoxy-5-oxopentanamido)pent-4-ynoate(1423324-26-8)

Safety Data

• Hazardous Substances Data: 1423324-26-8(Hazardous Substances Data)

Upstream product

• 1423324-25-7 (S)-methyl 2-((S)-2-amino-5-methoxy-5-oxopentanamido)pent-4-ynoate trifluoroacetate 
• 1046806-28-3 N²,N,N-dimethylaminomethylene-10-formyl-pteroic acid 
• 1423324-23-5 (S)-methyl 2-((S)-2-((tert-butoxycarbonyl)-amino)-5-methoxy-5-oxopentanamido)pent-4-ynoate 
• 14406-17-8 N-(tert-butoxycarbonyl)glutamic acid α-methyl ester dicyclohexylammonium salt 
• 166271-28-9 (S)-1-methoxy-1-oxopent-4-yn-2-aminium chloride 

Relevant articles and documents

Comparative Studies of Three Pairs of α- And γ-Conjugated Folic Acid Derivatives Labeled with Fluorine-18

The folate receptor (FR) is upregulated in various epithelial cancer types (FR α-isoform), while healthy tissues show only restricted expression. FR-targeted imaging using folate radiopharmaceuticals is therefore a promising approach for the detection of FR-positive cancer tissue. Almost all folate-based radiopharmaceuticals have been prepared by conjugation at the γ-carboxylic functionality of the glutamate moiety of folic acid. In this work, three pairs of fluorinated α- and γ-conjugated folate derivatives were synthesized and their in vitro and in vivo properties compared. The syntheses of all six regioisomers were obtained in good chemical yields using a multistep synthetic approach including the highly selective Cu(I)-catalyzed 1,3-dipolar cycloaddition. The radiosyntheses of the α- and γ-conjugated 18F-labeled folate derivatives were accomplished in moderate to good radiochemical yields, high radiochemical purities (>95%), and specific activities ranging from 25 to 196 GBq/μmol. In vitro, all folate derivatives showed high binding affinity to the FR-α (IC50 = 1.4-2.2 nM). In vivo PET imaging and biodistribution studies in FR-positive KB tumor-bearing mice demonstrated similar FR-specific tumor uptake for both regioisomers of each pair of compounds. However, FR-unspecific liver uptake was significantly lower for the α-regioisomers compared to the corresponding γ-regioisomers. In contrast, kidney uptake was up to 50% lower for the γ-regioisomers than for the α-regioisomers. These results show that the site of conjugation in the glutamyl moiety of folic acid has a significant impact on the in vivo behavior of 18F-based radiofolates, but not on their in vitro FR-binding affinity. These findings may potentially stimulate new directions for the design of novel 18F-labeled folate-based radiotracers.