21027-01-0

Basic information

• Product Name: Z-ALA-PRO-OH
• Synonyms: CBZ-L-ALA-PRO;Z-ALA-PRO-OH;Z-L-ALANYL-L-PROLINE;N-cbz-ala-pro;NSC 333444;N-Benzyloxycarbonyl-L-alanyl-L-proline;Cbz-Ala-Pro-OH
• CAS NO: 21027-01-0
• Molecular Formula: C₁₆H₂₀N₂O₅
• Molecular Weight: 320.34
• Mol File: 21027-01-0.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 576.4°Cat760mmHg
• Flash Point: 302.4°C
• Appearance: /
• Density: 1.301g/cm³
• Vapor Pressure: 3.99E-14mmHg at 25°C
• Refractive Index: 1.572
• Storage Temp.: -15°C
• CAS DataBase Reference: Z-ALA-PRO-OH(CAS DataBase Reference)
• NIST Chemistry Reference: Z-ALA-PRO-OH(21027-01-0)
• EPA Substance Registry System: Z-ALA-PRO-OH(21027-01-0)

Safety Data

• Hazardous Substances Data: 21027-01-0(Hazardous Substances Data)

Usage

General Description

Z-ALA-PRO-OH is a chemical compound that consists of the amino acids alanine (Ala) and proline (Pro) linked together, with a Z-protecting group attached to the amino group of the alanine residue. Z-ALA-PRO-OH is often used in the field of organic synthesis and peptide chemistry as a building block for creating longer peptides and proteins. The Z-protecting group helps to prevent unwanted side reactions during the synthesis process by blocking the reactivity of the amino group, allowing for more precise control over the assembly of the desired peptide sequence. Z-ALA-PRO-OH may also have potential applications in the development of new pharmaceuticals and bioactive compounds.

InChI:InChI=1/C16H20N2O5/c1-11(14(19)18-9-5-8-13(18)15(20)21)17-16(22)23-10-12-6-3-2-4-7-12/h2-4,6-7,11,13H,5,8-10H2,1H3,(H,17,22)(H,20,21)

Upstream product

• 147-85-3 L-proline 
• 33305-75-8 L-proline ethyl ester monohydrochloride 
• 474316-88-6 Fmoc-Pro-NHNHPh 
• 153240-03-0 H-Pro-NHNHPh 
• 71989-31-6 Fmoc-Pro-OH 
• 28861-55-4 Z-Ala-NHNHPh 
• 1142-20-7 N-Cbz-Ala 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 820239-42-7 benzyl N-[(1S)-2-(1H-1,2,3-benzotriazol-1-yl)-1-methyl-2-oxoethyl]carbamate 
• 226543-68-6 Z-Ala-Pro-NHNHPh 
• 3401-36-3 (N-benzyloxycarbonyl)-L-alanine N-hydroxysuccinimide ester 
• 1168-87-2 benzyloxycarbonylalanine p-nitrophenyl ester 
• 27544-35-0 Cbz-L-Ala-L-Pro-O^tBu 
• 474316-85-3 (S)-tert-butyl 2-(2-phenylhydrazinecarbonyl)pyrrolidine-1-carboxylate 

Downstream Products

• 22610-33-9 (2S,2'S)-N-(N-Benzyloxycarbonylalanyl)proline methyl ester 
• 1140836-14-1 (2S,3R)-tert-butyl 3-(benzyloxy)-2-((S)-1-((S)-2-(benzyloxycarbonylamino)propanoyl)-N-methylpyrrolidine-2-carboxamido)butanoate 
• 1403476-84-5 C₂₄H₂₉N₃O₄ 
• 66412-10-0 N-benzyloxycarbonyl-L-alanyl-L-proline anilide 
• 66382-56-7 N-benzyloxycarbonyl-L-alanyl-L-proline 4-nitroanilide 
• 66383-09-3 Benzyloxycarbonylalanyl-proline Ethylamide 
• 5565-29-7 L-alanyl-L-proline t-butylester 
• 29375-30-2 (S)-alanyl-(S)-proline tert-butyl ester 
• 108074-21-1 Z-Ala-Pro-Phe 
• 73535-26-9 Z-Ala-Pro-Pro-Pro-NHNHBoc 
• 75893-20-8 Z-Ala-Pro-Pro-Pro-OH 
• 75893-19-5 Z-Ala-Pro-NHNH₂ 
• 120791-98-2 N-(Benzyloxycarbonyl)-L-alanyl-L-prolyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-α-D-galactopyranosyl)-L-threonyl-O-tert-butyl-L-seryl-O-tert-butyl-L-seryl-O-tert-butyl-L-serin-tert-butylester 
• 120792-21-4 C₅₆H₆₆N₄O₂₃ 

Relevant articles and documents

3-Azaspiro[5,5]undecan-2,4-dioxo-3-yl diphenyl phosphate (ASUD-diphenyl phosphate), a new reagent for the synthesis of the N-protected amino acid-ASUD ester

A new reagent, 3-azaspiro[5,5]undecan-2,4-dioxo-3-yl diphenyl phosphate (ASUD-diphenyl phosphate) is described for the synthesis of N-protected amino acid-ASUD esters which are active esters useful in the synthesis of peptides. This compound was synthesized by reacting N-hydroxy-3-azaspiro[5,5]undecane-2,4-dione (HO-ASUD) with diphenyl chlorophosphate in the presence of a base at room temperature and was obtained in high yields. The ASUD-diphenyl phosphate reagent reacts with N-protected amino acids under mild conditions to give the corresponding ASUD active esters, while preserving the enantiomeric purity of the amino acid. The new reagent is a stable crystalline compound and eliminates the need for DCC, a potent skin allergen, used previously for the synthesis of N-protected amino acid-ASUD ester.

Convenient synthesis of C-terminal di- and tri-peptide amides from N-protected dipeptidoylbenzotriazoles

N-Protected dipeptidoylbenzotriazoles react with aqueous ammonia to give dipeptide primary amides (77-98%) and with N-unprotected α-amino amides to afford tripeptide primary amides (82-86%).

Efficient peptide coupling involving sterically hindered amino acids

(Chemical Equation Presented) Hindered amino acids have been introduced into peptide chains by coupling N-(Cbz- and Fmoc-α-aminoacyl) benzotriazoles with amino acids, wherein at least one of the components was sterically hindered, to provide compounds 3a-e, (3c +3 c′), 5a-d, (5a + 5a′), 6a-c, (6b + 6b′), 8a-c, 9a-e, 10a-d, and (10a + 10a′) in isolated yields of 41-95% with complete retention of chirality as evidenced by NMR and HPLC analysis. The benzotriazole activation methodology is a new route for the synthesis of sterically hindered peptides. (Note: compound numbers written within brackets represent diastereomeric mixtures or racemates; compound numbers without brackets represent enantiomers.)