1160-54-9

Basic information

• Product Name: Z-GLY-PRO-OH
• Synonyms: Z-GLY-PRO;Z-GLY-PRO-OH;Z-GLYCYL-L-PROLINE;Z-L-GLYCYL-L-PROLINE;N-BENZYLOXYCARBONYLGLYCYL-L-PROLINE;N-CARBOBENZOXYGLYCYL-L-PROLINE;BENZYLOXYCARBONYLGLYCYL-L-PROLINE;1-[N-[(phenylmethoxy)carbonyl]glycyl]-L-proline
• CAS NO: 1160-54-9
• Molecular Formula: C₁₅H₁₈N₂O₅
• Molecular Weight: 306.31
• EINECS: 214-598-8
• Mol File: 1160-54-9.mol
• Article Data: 14

Chemical Properties

• Melting Point: 155-158 °C
• Boiling Point: 579.8 °C at 760 mmHg
• Flash Point: 304.4 °C
• Appearance: /
• Density: 1.335 g/cm³
• Vapor Pressure: 2.77E-14mmHg at 25°C
• Refractive Index: 1.581
• Storage Temp.: −20°C
• PKA: 3.51±0.20(Predicted)
• BRN: 94536
• CAS DataBase Reference: Z-GLY-PRO-OH(CAS DataBase Reference)
• NIST Chemistry Reference: Z-GLY-PRO-OH(1160-54-9)
• EPA Substance Registry System: Z-GLY-PRO-OH(1160-54-9)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 1160-54-9(Hazardous Substances Data)

Usage

General Description

Z-GLY-PRO-OH is a chemical compound consisting of three amino acids: glycine, proline, and hydroxyproline, which are linked together by peptide bonds. It belongs to the class of zwitterionic compounds and contains a zwitterionic form of glycine. Z-GLY-PRO-OH plays a crucial role in biochemical and pharmaceutical research, particularly in the study of peptide structures and functions. It is commonly used as a building block for the synthesis of various peptides and proteins and has potential applications in drug development and therapeutic interventions. Additionally, Z-GLY-PRO-OH has been found to exhibit interesting chemical and biological properties, making it a valuable tool for investigating the structure-activity relationships of peptides. Overall, Z-GLY-PRO-OH is a versatile compound with significant implications in the fields of chemistry, biochemistry, and pharmacology.

InChI:InChI=1/C15H18N2O5/c18-13(17-8-4-7-12(17)14(19)20)9-16-15(21)22-10-11-5-2-1-3-6-11/h1-3,5-6,12H,4,7-10H2,(H,16,21)(H,19,20)/t12-/m0/s1

Upstream product

• 15050-24-5 N-(benzyloxycarbonyl)glycyl chloride 
• 147-85-3 L-proline 
• 2899-60-7 Cbz-Gly-ONSuc 
• 2899-57-2 Sphenyl N-benzyloxycarbonylaminoethanothioate 
• 16652-71-4 benzyl (2S)-2-pyrrolidinecarboxylate hydrochloride 
• 1138-80-3 N-(Benzyloxycarbonyl)glycine 
• 65022-15-3 benzyloxycarbonylglycyl-proline 4-nitranilide 
• 501-53-1 benzyl chloroformate 
• 173459-80-8 benzyl [2?(1H?benzo[d][1,2,3]triazol?1?yl)?2?oxoethyl]carbamate 
• 66449-90-9 (2S)-N-(N-Benzyloxycarbonylglycyl)proline methyl ester 
• 148205-60-1 Z-Gly-ONA 
• 120584-16-9 3-(Z-Gly)-methylpyridinium iodide ester 
• 1738-86-9 Z-Gly-ONp 
• 2778-21-4 3-(Z-Gly)-pyridyl ester 

Downstream Products

• 915958-58-6 C₂₇H₃₃N₃O₆ 
• 98807-41-1 C₂₀H₂₆N₂O₇ 
• 148205-94-1 Z-Gly-Pro-Arg(Tis)-Pro-NHNHBoc 
• 129720-87-2 Z-Gly-Pro-Arg(Mts)-Pro-cyclohexylamine 
• 134303-71-2 Z-Gly-Pro-Arg(NO₂)-OBzl 
• 134303-85-8 Z-Gly-Pro-Arg(Mts)-p-nitroaniline 
• 134303-82-5 Z-Gly-Pro-Arg(Mts)-cyclohexylamine 
• 120615-00-1 Z-Gly-Pro-Arg(Mts)-hexamethyleneimine 
• 134303-84-7 Z-Gly-Pro-Arg(NO₂)-aniline 
• 134303-81-4 Z-Gly-Pro-Arg(NO₂)-3-methylpiperidine 
• 134303-79-0 Z-Gly-Pro-Arg(NO₂)-piperidine 
• 134303-77-8 Z-Gly-Pro-Arg(NO₂)-N(C₃H₇)2 
• 134303-76-7 Z-Gly-Pro-Arg(NO₂)-N(C₂H₅)2 
• 134303-75-6 Z-Gly-Pro-Arg(NO₂)-N(CH₃)2 

Relevant articles and documents

Collision-induced dissociative chemical cross-linking reagent for protein structure characterization: Applied Edman chemistry in the gas phase

Chemical cross-linking combined with a subsequent enzymatic digestion andmass spectrometric analysis of the created crosslinked products presents an alternative approach to assess low-resolution protein structures and to gain insight into protein interfaces. In this contribution, we report the design of an innovative cross-linker based on Edman degradation chemistry, which leads to the formation of indicative mass shifted fragment ions and constant neutral losses (CNLs) in electrospray ionization (ESI)-tandem-mass spectrometry (MS/MS) product ion mass spectra, allowing an unambiguous identification of cross-linked peptides. Moreover, the characteristic neutral loss reactions facilitate automated analysis by multiple reaction monitoring suited for high throughput studies with good sensitivity and selectivity. The functioning of the novel cross-linker relies on the presence of a highly nucleophilic sulfur in a thiourea moiety, safeguarding for effective intramolecular attack leading to predictive and preferred cleavage of a glycyl-prolyl amide bond. Our innovative analytical concept and the versatile applicability of the collision-induced dissociative chemical cross-linking reagent are exemplified for substance P, luteinizing hormone releasing hormone LHRH and lysozyme. The novel cross-linker is expected to have a broad range of applications for probing protein tertiary structures and for investigating protein-protein interactions. Copyright

An unusual side reaction of 1-succinimidyl esters during peptide synthesis.

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Inhibition of prolyl oligopeptidase with a synthetic unnatural dipeptide

A new inhibitor, containing a linked proline-piperidine structure, for the enzyme prolyl oligopeptidase (POP) has been synthesised and demonstrated to bind covalently with the enzyme at the active site. This provides evidence that covalent inhibitors of P

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.)