60058-69-7

Basic information

• Product Name: (tert-butyloxycarbonyl)-β-benzyl-L-aspartyl-L-phenylalanine amide
• Synonyms: (tert-butyloxycarbonyl)-β-benzyl-L-aspartyl-L-phenylalanine amide
• CAS NO: 60058-69-7
• Molecular Weight: 469.538
• Mol File: 60058-69-7.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: (tert-butyloxycarbonyl)-β-benzyl-L-aspartyl-L-phenylalanine amide(CAS DataBase Reference)
• NIST Chemistry Reference: (tert-butyloxycarbonyl)-β-benzyl-L-aspartyl-L-phenylalanine amide(60058-69-7)
• EPA Substance Registry System: (tert-butyloxycarbonyl)-β-benzyl-L-aspartyl-L-phenylalanine amide(60058-69-7)

Safety Data

• Hazardous Substances Data: 60058-69-7(Hazardous Substances Data)

Upstream product

• 7536-58-5 BOC-L-aspartic acid 4-benzyl ester 
• 5241-58-7 L-Phenylalanine amide 
• 65864-22-4 (S)-2-amino-3-phenylpropionamide hydrochloride 
• 51987-73-6 (S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester 
• 88463-18-7 (S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropionamide 
• 222641-23-8 N-[(1,1-dimethylethoxy)carbonyl]-(L)-α-aspartyl-(L)-phenylalaninamide mono(sodium) salt 
• 100-39-0 benzyl bromide 
• 13798-75-9 N^α-t-butoxycarbonylaspartic acid α-N-hydroxysuccinimide ester β-benzyl ester 
• 24730-33-4 (S)-2-amino-3-phenylpropanamide hydrobromide 

Downstream Products

• 114671-23-7 Boc-D-Asp(Phe-NH₂)-piperidide 
• 88121-98-6 Boc-L-Asp(Phe-NH₂)-piperidide 
• 114671-22-6 Boc-D-Asp(piperidide)-Phe-NH₂ 
• 88121-97-5 Boc-L-Asp(piperidide)-Phe-NH₂ 
• 60058-91-5 H-Asp(OBn)-Phe-NH₂ trifluoroacetate 
• 5534-95-2 pentagastrin 
• 5549-51-9 H-Met-Asp(OBzl)-Phe-NH₂ 
• 60369-28-0 H₂N-Trp-Met-Asp(Bzl)-Phe-NH₂ 
• 88463-49-4 C₄₄H₅₅N₇O₉S 
• 27168-83-8 Boc-Trp-Lys-Asp-Phe-NH₂ 
• 131450-41-4 (S)-3-{(S)-6-Benzyloxycarbonylamino-2-[(S)-2-tert-butoxycarbonylamino-3-(1H-indol-3-yl)-propionylamino]-hexanoylamino}-N-((S)-1-carbamoyl-2-phenyl-ethyl)-succinamic acid benzyl ester 
• 131450-19-6 Boc-Trp-homolysine(N^ω-2-methylphenylaminocarbonyl)-Asp-Phe-NH2 
• 131450-40-3 H-Lys(CBz)-Asp(OBn)-Phe-NH₂ hydrochloride 
• 131450-16-3 Boc-Trp-Orn(N^γ-2-methylphenylaminocarbonyl)-Asp-Phe-NH2 

Relevant articles and documents

Microwave-assisted solution phase peptide synthesis in neat water

An environmentally benign protocol for solution phase peptide synthesis has been developed in neat water using TBTU/HOBt/DIEA as a coupling combination under microwave irradiation. Key features of this procedure are the replacement of commonly used toxic organic solvents like DMF and NMP, the use of lower amounts of reactants, compatibility with both N-α-Boc- and N-α-Fmoc-protected amino acids and all commonly used side-chain protective groups, short reaction time, and racemization-free synthesis in high yield and purity. The Royal Society of Chemistry 2013.

Development of peptide 3D structure mimetics: Rational design of novel peptoid cholecystokinin receptor antagonists

The two hormones cholecystokinin and gastrin share the same C-terminal sequence of amino acids, namely Gly29-Trp30-Met31-Asp32-Phe33-NH2. Nevertheless, this congruence has not precluded usi

CCK-B agonist or antagonist activities of structurally hindered and peptidase-resistant Boc-CCK4 derivatives

Replacement of Met31 by (N-Me)Nle in CCK8 or CCK4 has been shown to improve the affinity and selectivity for CCK-B receptors. In order to obtain molecules with enhanced bioavailability, two novel series of protected tetrapeptides of the general formula Boc-Trp30-X-Asp-Y33 have been developed. Introduction of (N-Me)Nle and the bulky, aromatic naphthylalaninamide (Nal-NH2) in positions X and Y, respectively, does not greatly modify the affinity for guinea pig brain CCK-B receptors. In contrast, incorporation of hindering N-methyl amino acids such as (N-Me)Phe, (N-Me)Phg, or (N-Me)Chg, but not their non-methylated counterparts, in position X induced a large decrease in affinity for the CCK-B binding sites. Among the various peptides synthesized, Boc-[(N-Me)Nle31,1Nal- NH233]CCK4 (2) (K(I) = 2.8 nM), Boc-[Phg31,1Nal-NH233]CCK4 (15) (K(I) = 14 nM), and Boc-[Phg31,1Nal-N(CH3)233]CCK4 (17) (K(I) = 39 nM) displayed good affinities for brain CCK-B receptors and had good selectivity ratios. These pseudopeptides, in which the presence of unnatural and hydrophobic residues is expected to improve their penetration of the central nervous system, were shown to be very resistant to brain peptidases. Interestingly, whereas compounds 2 and 15 proved to be full agonists for rat hippocampal CCK-B receptors when measured in an electrophysiological assay, compound 17 behaved as a potent antagonist in the same test and displayed a good affinity in rat brain K(I)(CCK-B) = 51 nM as compared to the Merck antagonist L365,260, K(I)(CCK-B) = 12 nM. This illustrates a simple means to obtain CCK-B antagonists and suggests that the free, CONH2 group plays a critical role in the recognition of the agonist state of brain CCK-B receptors.