914459-77-1

Basic information

• Product Name: (4-{(S)-2-Amino-2-[1-((S)-2-carbamoyl-1-pent-4-ynylcarbamoyl-ethylcarbamoyl)-cyclohexylcarbamoyl]-ethyl}-benzyl)-phosphonic acid di-tert-butyl ester
• Synonyms: (4-{(S)-2-Amino-2-[1-((S)-2-carbamoyl-1-pent-4-ynylcarbamoyl-ethylcarbamoyl)-cyclohexylcarbamoyl]-ethyl}-benzyl)-phosphonic acid di-tert-butyl ester
• CAS NO: 914459-77-1
• Molecular Weight: 675.806
• Mol File: 914459-77-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (4-{(S)-2-Amino-2-[1-((S)-2-carbamoyl-1-pent-4-ynylcarbamoyl-ethylcarbamoyl)-cyclohexylcarbamoyl]-ethyl}-benzyl)-phosphonic acid di-tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (4-{(S)-2-Amino-2-[1-((S)-2-carbamoyl-1-pent-4-ynylcarbamoyl-ethylcarbamoyl)-cyclohexylcarbamoyl]-ethyl}-benzyl)-phosphonic acid di-tert-butyl ester(914459-77-1)
• EPA Substance Registry System: (4-{(S)-2-Amino-2-[1-((S)-2-carbamoyl-1-pent-4-ynylcarbamoyl-ethylcarbamoyl)-cyclohexylcarbamoyl]-ethyl}-benzyl)-phosphonic acid di-tert-butyl ester(914459-77-1)

Safety Data

• Hazardous Substances Data: 914459-77-1(Hazardous Substances Data)

Upstream product

• 15252-44-5 1-amino-pent-4-yne 
• 914459-76-0 {4-[2-[1-(2-carbamoyl-1-pent-4-ynylcarbamoyl-ethylcarbamoyl)-cyclohexylcarbamoyl]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-ethyl]-benzyl}-phosphonic acid di-tert-butyl ester 
• 914459-75-9 [1-(2-carbamoyl-1-pent-4-ynylcarbamoyl-ethylcarbamoyl)-cyclohexyl]-carbamic acid 9H-fluoren-9-ylmethyl ester 
• 914459-73-7 (2-carbamoyl-1-pent-4-ynylcarbamoyl-ethyl)-carbamic acid tert-butyl ester 
• 914459-74-8 2-amino-N¹-pent-4-ynyl-succinamide 

Downstream Products

• 914459-90-8 (4-{(S)-2-Amino-2-[1-((S)-2-carbamoyl-1-pentylcarbamoyl-ethylcarbamoyl)-cyclohexylcarbamoyl]-ethyl}-benzyl)-phosphonic acid di-tert-butyl ester 
• 914459-92-0 (4-{(S)-2-Acetylamino-2-[1-((S)-2-carbamoyl-1-pent-4-ynylcarbamoyl-ethylcarbamoyl)-cyclohexylcarbamoyl]-ethyl}-benzyl)-phosphonic acid di-tert-butyl ester 
• 914459-91-9 (4-{(S)-2-(2-Azido-acetylamino)-2-[1-((S)-2-carbamoyl-1-pentylcarbamoyl-ethylcarbamoyl)-cyclohexylcarbamoyl]-ethyl}-benzyl)-phosphonic acid di-tert-butyl ester 
• 914459-79-3 (4-{(S)-2-(2-Azido-acetylamino)-2-[1-((S)-2-carbamoyl-1-pent-4-ynylcarbamoyl-ethylcarbamoyl)-cyclohexylcarbamoyl]-ethyl}-benzyl)-phosphonic acid di-tert-butyl ester 

Relevant articles and documents

Application of azide-alkyne cycloaddition 'click chemistry' for the synthesis of Grb2 SH2 domain-binding macrocycles

Copper (I) promoted [3+2] Huisgen cycloaddition of azides with terminal alkynes was used to prepare triazole-containing macrocycles based on the Grb2 SH2 domain-binding motif, 'Pmp-Ac6c-Asn', where Pmp and Ac6c stand for 4-phosphonomethylphenylalanine and 1-aminocyclohexanecarboxylic acid, respectively. When cycloaddition reactions were conducted at 1 mM substrate concentrations, cyclization of monomeric units occurred. At 2 mM substrate concentrations the predominant products were macrocyclic dimers. In Grb2 SH2 domain-binding assays the monomeric (S)-Pmp-containing macrocycle exhibited a Kd value of 0.23 μM, while the corresponding dimeric macrocycle was found to have greater than 50-fold higher affinity. The open-chain dimer was also found to have affinity equal to the dimeric macrocycle. This work represents the first application of 'click chemistry' to the synthesis of SH2 domain-binding inhibitors and indicates its potential utility.