105414-01-5

Basic information

• Product Name: Cbz-L-Pro-OCO₂-i-Bu
• CAS NO: 105414-01-5
• Molecular Weight: 349.384
• Mol File: 105414-01-5.mol

Chemical Properties

• CAS DataBase Reference: Cbz-L-Pro-OCO₂-i-Bu(CAS DataBase Reference)
• NIST Chemistry Reference: Cbz-L-Pro-OCO₂-i-Bu(105414-01-5)
• EPA Substance Registry System: Cbz-L-Pro-OCO₂-i-Bu(105414-01-5)

Safety Data

• Hazardous Substances Data: 105414-01-5(Hazardous Substances Data)

Upstream product

• 108-23-6 isopropyl chloroformate 
• 1148-11-4 N-Benzyloxycarbonyl-L-proline 
• 501-53-1 benzyl chloroformate 
• 543-27-1 isobutyl chloroformate 

Downstream Products

• 208453-17-2 (S)-2-Ethylsulfanylcarbonyl-pyrrolidine-1-carboxylic acid benzyl ester 
• 23631-72-3 N-carbobenzoxy-L-prolyl-L-phenylalanine methyl ester 
• 54793-80-5 (S)-proline-(S)-phenylalanine methyl ester 
• 60242-12-8 C₂₂H₂₄N₂O₅ 
• 6686-03-9 (S)-benzyl 2-(((S)-3-(1H-indol-3-yl)-1-methoxy-1-oxopropan-2-yl)carbamoyl)pyrrolidine-1-carboxylate 
• 17350-17-3 (S)-2-[(S)-1-(benzyloxycarbonyl)pyrrolidine-2-carboxamido]-3-phenylpropanoic acid 
• 6216-63-3 N-Cbz-Prolinol 
• 132168-71-9 Z-Pro-D-Phe-NHMe 
• 132168-72-0 Z-Pro-D-Val-NHMe 
• 132168-70-8 Z-Pro-D-Ala-NHMe 
• 146349-27-1 methyl 3(R)-<<<1-(benzyloxycarbonyl)-2(S)-pyrrolidinyl>carbonyl>amino>-2-oxo-1-azetidineacetate 
• 146349-35-1 4(R)-<<<1-(benzyloxycarbonyl)-2(S)-pyrrolidinyl>carbonyl>amino>-3-oxo-2-isoxazolidine 
• 107994-40-1 N_α-(Benzyloxycarbonyl-L-prolyl)-D,L-4-cyanphenylalanin 
• 127331-68-4 Z-Pro-D-Hph-Gly-NH₂ 

Relevant articles and documents

Efficient ball-mill procedure in the 'green' asymmetric aldol reaction organocatalyzed by (S)-proline-containing dipeptides in the presence of water

The organocatalytic activity of (S)-proline-based dipeptides 1a-c has been evaluated in the asymmetric aldol reaction between representative ketones with various aromatic aldehydes under solvent-free conditions in a ball mill. In particular, the methyl ester of (S)-proline-(S)-tryptophan, (S,S)-1c, proved to be an efficient organocatalyst, and the aldol reaction proceeded with good chemical yields and excellent diastereo- and enantioselectivity (up to 98:2 anti/syn dr and up to 98% ee), in the presence of water, and 5 mol % of benzoic acid as additive.

α-N-Protected dipeptide acids: A simple and efficient synthesis via the easily accessible mixed anhydride method using free amino acids in DMSO and tetrabutylammonium hydroxide

The importance of dipeptides both in medicinal and pharmacological fields is well documented and many efforts have been made to find simple and efficient methods for their synthesis. For this reason, we have investigated the synthesis of α-N-protected dipeptide acids by reacting the easily accessible mixed anhydride of α-N-protected amino acids with free amino acids under different reaction conditions. The combination of TBA-OH and DMSO has been found to be the best to overcome the low solubility of amino acids in organic solvents. Under these experimental conditions, the homogeneous phase condensation reaction occurs rapidly and without detectable epimerization. The present method is also applicable to side-chain unprotected Tyr, Trp, Glu, and Asp but not Lys. This latter residue is able to engage two molecules of mixed anhydride giving the corresponding isotripeptide. Moreover, the applicability of this protocol for the synthesis of tri- and tetrapeptides has been tested. This approach reduces the need for protecting groups, is cost effective, scalable, and yields dipeptide acids that can be used as building blocks in the synthesis of larger peptides.

A chiral amino-naphthalene-derived prolinamide catalyst for the enantioselective Michael addition of ketones to nitroolefins

An enantioselective Michael addition of ketones to nitroolefins has been accomplished using a novel chiral aminonaphthalenederived prolinamides catalyst 1. The desired Michael adducts were obtained in high yields (up to 93%) as well as good diastereoselectivities (>99:1) and enantioselectivities (48%-99% ee).

IMIDAZOPYRIDINE INHIBITORS OF IAP

The invention provides novel inhibitors of IAP that are useful as therapeutic agents for treating malignancies where the compounds have the general formula I: wherein Q, X1, X2, Y, Z R1, R2, R3, R3', R4, R4', R5, R6, R6' and n are as described herein.

Reduction of ethanethiol esters to aldehydes

Reduction of ethanethiol esters of α-amino acids to α-amino aldehydes by triethylsilane and catalytic palladium-on-carbon is described. α-Amino aldehydes with Boc, Cbz, or Fmoc protection could be obtained without racemization in high yield.

Synthesis and dopamine receptor modulating activity of lactam conformationally constrained analogues of Pro-Leu-Gly-NH2

A series of analogues of the potent analogue of Pro-Leu-Gly-NH2 (PLG), 2- oxo-3(R)-[(2(S)-pyrrolidinylcarbonyl)amino]-1-pyrrolidineacetamide (2) were synthesized in which the (R)-γ-lactam residue of 2 was replaced with a (R)- β-lactam, (R)-aminosuccinimide, (R)-cycloseryl, (R)-δ-lactam, (R)-ε- lactam, or (S)-ε-lactam residue to give analogues 3-8, respectively. These substitutions were made so as to vary the ψ2 torsion angle. The analogues were tested for their ability to enhance the binding of the dopamine receptor agonist ADTN to the dopamine receptor. Analogues 3-6 and 8 exhibited dose- response curves that were bell-shaped in nature with the maximum effect occurring at a concentration of 1 μM. Analogue 7 was inactive. Analogues 3 and 4 were found to be as effective as PLG, while analogues 5, 6, and 8 appeared to be more effective than PLG in terms of enhancing the binding of ADTN to dopamine receptors. The activity of analogues 3-6 and 8 with their ψ2 angles in the vicinity of that observed in a type II β-turn is consistent with the hypothesis that this type of turn is the bioactive conformation of PLG.

Amino acids and peptides. XVI. Synthesis of N-terminal tetrapeptide analogs of fibrin α-chain and their inhibitory effects on fibrinogen/thrombin clotting

N-Terminal tetrapeptide analogs of fibrin α-chain were synthesized by the solution method using a new active ester, the ester of the oxime of p-nitroacetophenone, and by the solid-phase method. Their inhibitory effects on fibrinogen/thrombin clotting were examined. Of the synthetic peptides, amide analogs of Gly-Pro-Arg-Pro exhibited a more potent inhibitory effect.

A facile synthesis of chiral N-protected β-amino alcohols

Chiral N-protected β-amino alcohols are easily obtained by NaBH4 reduction of mixed anhydrides of N-protected α-amino acids in an organic/aqueous medium. The alcohols obtained from side chain or main chain reduction of N-protected aspartic acid are converted in good yields into lactones.

Synthesis and Biological Evaluation of Analogues of Pro-Leu-Gly-NH2 Modified at the Leucyl Residue

A series of analogues of Pro-Leu-Gly-NH2 (PLG) in which the leucine residue has been replaced with the aliphatic amino acids L-isoleucine, L-2-aminohexanoic acid (Ahx), L-2-aminopentanoic acid, and L-2-aminobutanoic acid and the aromatic amino acids L-phenylalanine, L-phenylglycine, L- and D-2-amino-4-phenylbutanoic acid, L-O-methyltyrosine, and L-4-nitrophenylalanine have been synthesized.These analogues were tested for their ability to enhance the binding of the dopamine receptor agonist 2-amino-6,7-dihydroxy-1,2,3,4-tetrahydronaphthalene (ADTN) to striatal dopamine receptors.Two of the abov e analogues, Pro-Ahx-Gly-NH2 (3) and Pro-Phe-Gly-NH2 (6), showed significant activity in this assay system.Pro-Ahx-Gly-NH2 produced a 16percent enhancement of ADTN binding at 0.1 μM, while Pro-Phe-Gly-NH2 enhanced the binding of ADTN by 31percent at a concentration of 1 μM.

Conformational Investigations of α,β-Dehydropeptides. I. Synthesis of Model Dipeptides

Three series of model dipeptides: Ac-Pro-X-NHMe, where X = L-, D- and Δ-Ala, L-, D- and (Z)-Δ-Phe and L-, D- and Δ-Val, designed for conformational investigation of α,β-dehydroamino acid effect on peptide chain β-turn have been synthesized.