446880-45-1

Basic information

• Product Name: 3-amino-N-tert-butoxycarbonylmethyl-N-{2-[(1-carbamoyl-2-phenyl-ethyl)-carboxyacetyl-amino]-ethyl}-succinamic acid cyclohexyl ester
• Synonyms: 3-amino-N-tert-butoxycarbonylmethyl-N-{2-[(1-carbamoyl-2-phenyl-ethyl)-carboxyacetyl-amino]-ethyl}-succinamic acid cyclohexyl ester
• CAS NO: 446880-45-1
• Molecular Weight: 604.701
• Mol File: 446880-45-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 3-amino-N-tert-butoxycarbonylmethyl-N-{2-[(1-carbamoyl-2-phenyl-ethyl)-carboxyacetyl-amino]-ethyl}-succinamic acid cyclohexyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3-amino-N-tert-butoxycarbonylmethyl-N-{2-[(1-carbamoyl-2-phenyl-ethyl)-carboxyacetyl-amino]-ethyl}-succinamic acid cyclohexyl ester(446880-45-1)
• EPA Substance Registry System: 3-amino-N-tert-butoxycarbonylmethyl-N-{2-[(1-carbamoyl-2-phenyl-ethyl)-carboxyacetyl-amino]-ethyl}-succinamic acid cyclohexyl ester(446880-45-1)

Safety Data

• Hazardous Substances Data: 446880-45-1(Hazardous Substances Data)

Upstream product

• 330187-60-5 2(S)-[N-[2-[N'-(9-fluorenylmethoxycarbonyl)-N'-(tert-butyloxycarbonylmethyl)]aminoethyl]-N-[(1',3'-dioxo-3'-benzyloxy)propyl]]-2-amino-3-phenylpropionamide 
• 330187-58-1 3-phenyl-1(S)-[[2'-[N''-(9-fluorenylmethoxycarbonyl)-N''-(tert-butyloxycarbonylmethyl)]amino]ethylamino]propionamide 
• 446880-44-0 2(S)-[N-[2-[N'-(tert-butyloxycarbonylmethyl)]aminoethyl]-N-[(1',3'-dioxo-3'-benzyloxy)propyl]]-2-amino-3-phenylpropionamide 
• 330187-54-7 N-(S-ethyl-thiocarbonylmethyl)-N-Fmoc-glycine tert-butyl ester 
• 330187-55-8 (9H-Fluoren-9-yl)methyl(tert-butoxycarbonyl)methylformylmethyl carbamate 
• 141743-16-0 N-(carboxymethyl)-N-Fmoc-glycine tert-butyl ester 
• 65864-22-4 (S)-2-amino-3-phenylpropionamide hydrochloride 
• 330187-62-7 N-{2-[benzyloxycarbonylacetyl-(1-carbamoyl-2-phenyl-ethyl)-amino]-ethyl}-3-benzyloxycarbonylamino-N-tert-butoxycarbonylmethyl-succinamic acid cyclohexyl ester 

Downstream Products

• 446880-48-4 [(S)-1-((S)-1-Acetylamino-2-phenyl-ethyl)-6-cyclohexyloxycarbonylmethyl-5,8,10-trioxo-[1,4,7]triazecan-4-yl]-acetic acid tert-butyl ester 
• 446880-50-8 [(S)-7-((S)-1-Amino-2-phenyl-ethyl)-4-tert-butoxycarbonylmethyl-3,8,10-trioxo-[1,4,7]triazecan-2-yl]-acetic acid cyclohexyl ester 
• 330187-64-9 [(S)-1-((S)-1-Carbamoyl-2-phenyl-ethyl)-6-cyclohexyloxycarbonylmethyl-5,8,10-trioxo-[1,4,7]triazecan-4-yl]-acetic acid tert-butyl ester 

Relevant articles and documents

Ni-to-Ni + 3-ethylene-bridged partially modified retro-inverso tetrapeptide β-turn mimetic: Design, synthesis, and structural characterizationt

A 10-membered heterocyclic ring system 1,3,8-trisubstituted 2,5,7-trioxo-1,4,8-triazadecane that represents a Ni-to-Ni + 3-ethylene-bridged partially modified retro-inverso tetrapeptide β-turn mimetic (EBRIT-BTM) has been designed, synthesized, and structurally analyzed. These compounds utilize an ethylene bridge to replace the COi · · · HNi + 3 10-membered hydrogen bond of standard β-turns. The N, N'-ethylene-bridged dimer was obtained in 90% yield by reductive alkylation of phenylalanylamide with a tert-butyl N-(9-fluorenylmethyloxycarbonyl), N-(2-formylmethyl)-glycinate. An orthogonal protection strategy and HATU-mediated couplings allowed efficient stepwise additions of monomeric building blocks leading to a Ni-to-Ni+3-ethylene-bridged linear precursor: H-Asp-(OcHex)-NGly-OBut HO2CCH2CO-NPhe-NH2. Further elaboration of the linear precursor generated the ethylene-bridged model compounds H2N-rPheN-mGly-Asp-NGly-OH (16) and Ac-gPheN-mGly-Asp-NGly-OH (18) (g, gem-diaminoalkyl; m, malonyl; and r, direction-reversed amino acid residue) in 44 and 39% yields, respectively. The structural features of the two EBRIT-BTM compounds were determined using 1H NMR and extensive computer simulations. The results indicate that the 10-membered rings are conformationally constrained with well-defined structural features and that the three amide bonds in the ring are in the trans orientation. The topological arrangement of the residues in the ring system closely resembles a type II' β-turn. Transformation of CONH2 in the N-terminal amino acid residue of 16 into NHCOCH3 in 18 resulted in the formation of a hydrogen bond between the NH ofgPhe-COCH3 and the C-terminal carboxyl of Gly, initiating an antiparallel β-sheet. The formulation of the concept applying a minimalistic structural elaboration approach and the synthetic exploration, together with the conformational analysis, offer a new molecular scaffolding system and a true tetrapeptide secondary structure mimetic that can be used to generate peptidomimetics of biological interest.