28944-94-7

Basic information

• Product Name: D-Alanine, N-[N-[(phenylmethoxy)carbonyl]-L-phenylalanyl]-, methyl ester
• CAS NO: 28944-94-7
• Molecular Formula: C21H24N2O5
• Molecular Weight: 384.432
• Mol File: 28944-94-7.mol
• Article Data: 32

Chemical Properties

• CAS DataBase Reference: D-Alanine, N-[N-[(phenylmethoxy)carbonyl]-L-phenylalanyl]-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: D-Alanine, N-[N-[(phenylmethoxy)carbonyl]-L-phenylalanyl]-, methyl ester(28944-94-7)
• EPA Substance Registry System: D-Alanine, N-[N-[(phenylmethoxy)carbonyl]-L-phenylalanyl]-, methyl ester(28944-94-7)

Safety Data

• Hazardous Substances Data: 28944-94-7(Hazardous Substances Data)

Upstream product

• 1161-13-3 N-Cbz-L-Phe 
• 2491-20-5 L-alanine methyl ester hydrochloride 
• 10065-72-2 L-Alanine methyl ester 
• 4816-89-1 Cbz-Phe-OCH₂CONH₂ 
• 122751-39-7 Z-Phe-OPyCl 
• 7625-53-8 D-alanine methyl ester 
• 35909-92-3 N-carbobenzoxy-L-phenylalanine methyl ester 
• 14316-06-4 D-alanine methyl ester hydrochloride 
• 501-53-1 benzyl chloroformate 
• 63-91-2 L-phenylalanine 
• 67-56-1 methanol 
• 65118-54-9 N-(benzyloxycarbonyl)phenylalanyl-alanine amide 
• 3588-57-6 Z-DL-Phe-OH 
• 133010-22-7 benzyl (S)-(1-fluoro-1-oxo-3-phenylpropan-2-yl)carbamate 

Downstream Products

• 65118-54-9 N-(benzyloxycarbonyl)phenylalanyl-alanine amide 
• 3338-39-4 N-benzyloxycarbonyl-L-phenylalanyl-L-alanine 
• 115514-18-6 (S)-methyl 2-(5-((S)-1-(((benzyloxy)carbonyl)amino)-2-phenylethyl)-1H-tetrazol-1-yl)propanoate 
• 223271-89-4 {(S)-1-[(S)-1-((S)-1-Carbamoyl-4-guanidino-butylcarbamoyl)-ethylcarbamoyl]-2-phenyl-ethyl}-carbamic acid benzyl ester 
• 143087-83-6 Z-L-Phe-L-Ala-L-Leu-NH₂ 
• 17563-25-6 N-benzyloxycarbonyl-L-phenylalanyl-D-alanine 
• 1432584-89-8 (Z)-N-((S)-2-((S)-2-(((benzyloxy)carbonyl)amino)-3-phenylpropanamido)propylidene)-2-(((S)-1-(tert-butoxy)-3-methyl-1-oxobutan-2-yl)amino)-2-oxoethanamine oxide 
• 1432584-90-1 (5S,8S,14S)-tert-butyl 5-benzyl-14-isopropyl-8-methyl-3,6,9,12-tetraoxo-1-phenyl-2-oxa-4,7,10,13-tetraazapentadecan-15-oate 
• 167498-27-3 AQ₅₇₃₁₈₈ 
• 106556-08-5 Z-L-Phe-L-Ala-OCam 
• 69193-13-1 Cbz-L-Phe-L-Leu-NH₂ 
• 167498-32-0 benzyl (S,S)-1-(1-hydroxypropan-2-ylamino)-1-oxo-3-phenylpropan-2-ylcarbamate 
• 80870-39-9 D-phenylalanine-L-alanine methylester 
• 3235-53-8 Z-Phe-Ala-NHNH₂ 

Relevant articles and documents

Development of a triazinedione-based dehydrative condensing reagent containing 4-(dimethylamino)pyridine as an acyl transfer catalyst

A new triazinedione-based reagent, (N,N′-dialkyl)triazinedione-4-(dimethylamino)pyridine (ATD-DMAP) was developed for the operationally simple dehydrative condensation of carboxylic acids. This reagent comprises an ATD core and DMAP as the leaving group, which is liberated into the reaction system to accelerate acyl transfer reactions. Upon adding ATD-DMAP to a mixture of carboxylic acids and alcohols in the presence of an amine base, the corresponding esters were formed rapidly at room temperature. Moreover, dehydrative condensation between carboxylic acids and amines using ATD-DMAP proceeded in high yield.

Trimodular Solution-Phase Protocol for Rapid Large-Scale Synthesis of Hydrogen Bond Surrogate-Constrained α-Helicomimics

Scalability, optimal reagent usage, high yields, easy isolation, and cost-effectiveness, are key for the applicability of synthetic methodologies in the production of potential therapeutics. Hydrogen bond surrogate (HBS) constrained α-helical peptides (α-helicomimics) have shown promise as therapeutics based on their efficiency to interfere with protein-biomolecular interactions. The propyl HBS-constrained α-helicomimics have shown the highest helicities in both single turn and extended, α-helices (STαH, EαH). Here we present a solution-phase synthetic (SPS) method, for the rapid, large-scale, low-cost synthesis of libraries of STαH and EαH in high yields. The key to efficiency is our trimodular (M1, M2, M3) synthetic protocol where M1 is a library of HBS-linked peptidomimetic synthons of both STαH and EαH; M2 and M3 are desired oligopeptide libraries. Advantages of the trimodular method over conventional unimodular methods are demonstrated through the synthesis of large-scale libraries of M1, STαH, and EαH.

A Bottom-Up Approach to Preserve Thioamide Residue Stereochemistry during Fmoc Solid-Phase Peptide Synthesis

Thioamides are useful biophysical probes for the study of peptide structure and folding. The α-C stereochemistry of thioamide amino acids, however, is easily epimerized during solid-phase peptide synthesis (SPPS), which limits the sequence space that is a