PROLINAMIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C5H10N2O
Molecular Weight	114.1457
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC(=O)[C@@H]1CCCN1

InChI

InChIKey=VLJNHYLEOZPXFW-BYPYZUCNSA-N

InChI=1S/C5H10N2O/c6-5(8)4-2-1-3-7-4/h4,7H,1-3H2,(H2,6,8)/t4-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C5H10N2O
Molecular Weight	114.1457
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Approval Year

PubMed

Title	Date	PubMed
Intramolecular hydrogen bond-controlled prolyl amide isomerization in glucosyl 3(S)-hydroxy-5-hydroxymethylproline hybrids: a computational study.	2010-09-09	20707355
The mimic of type II aldolases chemistry: asymmetric synthesis of beta-hydroxy ketones by direct aldol reaction.	2010-08	20572810
Chirally functionalized hollow nanospheres containing L-prolinamide: synthesis and asymmetric catalysis.	2010-07-12	20509127
Imidazolidinone intermediates in prolinamide-catalyzed aldol reactions.	2010-06-28	20461270
Influence of glucose-templated proline mimetics on the beta-turn conformation of the peptide fragment Ac-Leu-D-Phe-Pro-Val-NMe2 found in Gramicidin S.	2010-06-16	20399421
Enantioseparation of amino acids and alpha-hydroxy acids on ligand-exchange continuous beds by capillary electrochromatography.	2010-05	20422630
Conformational preferences and prolyl cis-trans isomerization of phosphorylated Ser/Thr-Pro motifs.	2010-04	19885922
Orexin receptor antagonism prevents transcriptional and behavioral plasticity resulting from stimulant exposure.	2010-01	19596018
Novel sulfur and selenium containing bis-alpha-amino acids from 4-hydroxyproline.	2010-01	19214702
Reoptimization of the AMBER force field parameters for peptide bond (Omega) torsions using accelerated molecular dynamics.	2009-12-31	19938868
Pre-steady-state kinetic analysis of cis-3-chloroacrylic acid dehalogenase: analysis and implications.	2009-12-15	19856961
Amide-based bifunctional organocatalysts in asymmetric reactions.	2009-11-07	19826653
The implications of (2S,4S)-hydroxyproline 4-O-glycosylation for prolyl amide isomerization.	2009-10-12	19739208
Cis-trans proline isomerization effects on collagen triple-helix stability are limited.	2009-09-30	19725497
Synthesis of acrylic polymer beads for solid-supported proline-derived organocatalysts.	2009-07-16	19522533
Direct aldol reactions catalyzed by intramolecularly folded prolinamide dendrons: dendrimer effects on stereoselectivity.	2009-06-14	19587933
Intramolecular hydrogen bond-controlled prolyl amide isomerization in glucosyl 3'(S)-hydroxy-5'-hydroxymethylproline hybrids: influence of a C-5'-hydroxymethyl substituent on the thermodynamics and kinetics of prolyl amide cis/trans isomerization.	2009-05-15	19354261
Conformational preferences of N-methoxycarbonyl proline dipeptide.	2009-05	18988252
Intra- and intermolecular interaction inducing pyramidalization on both sides of a proline dipeptide during isomerization: an ab initio QM/MM molecular dynamics simulation study in explicit water.	2009-04-01	19267429
Crystal structures and spectroscopic properties of ester amide and diamide of squaric acid with prolinamide.	2009-04	19101193
Design and synthesis of glucose-templated proline-lysine chimera: polyfunctional amino acid chimera with high prolyl cis amide rotamer population.	2009-03-31	19185292
Conformational preferences and cis-trans isomerization of L-3,4-dehydroproline residue.	2009	19373924
Inactivation of Cg10062, a cis-3-chloroacrylic acid dehalogenase homologue in Corynebacterium glutamicum, by (R)- and (S)-oxirane-2-carboxylate: analysis and implications.	2008-08-19	18646866
The rate enhancement for prolyl cis-to-trans isomerization of cyclic CPFC peptide is caused by an increase in the vibrational entropy of the transition state.	2008-03-20	18302366
Discovery of long-acting N-(cyanomethyl)-N-alkyl-L-prolinamide inhibitors of dipeptidyl peptidase IV.	2008-01-01	17962025
Highly enantioselective strecker reaction of ketoimines catalyzed by an organocatalyst from (S)-BINOL and L-prolinamide.	2008	18399513
Conformational preferences of pseudoproline residues.	2007-11-01	17927239
Effects of glycosylation of (2S,4R)-4-hydroxyproline on the conformation, kinetics, and thermodynamics of prolyl amide isomerization.	2007-09-26	17764180
Conformational preferences and cis-trans isomerization of azaproline residue.	2007-05-17	17439267
Synthesis of a new pi-deficient phenylalanine derivative from a common 1,4-diketone intermediate and study of the influence of aromatic density on prolyl amide isomer population.	2007	17143857
Organocatalytic highly enantioselective synthesis of secondary alpha-hydroxyphosphonates.	2006-10-12	17020334
Electronic control of amide cis-trans isomerism via the aromatic-prolyl interaction.	2006-02-22	16478167
Identification of a novel spiropiperidine opioid receptor-like 1 antagonist class by a focused library approach featuring 3D-pharmacophore similarity.	2006-02-09	16451050
Peptidyl-prolyl isomerase inhibitors.	2006	16302169
C2-symmetric bisprolinamide as a highly efficient catalyst for direct aldol reaction.	2005-11-10	16268568
Readily tunable and bifunctional L-prolinamide derivatives: design and application in the direct enantioselective Aldol reactions.	2005-09-29	16178579
Direct, facile aldehyde and ketone alpha-selenenylation reactions promoted by L-prolinamide and pyrrolidine sulfonamide organocatalysts.	2005-07-08	15989353
Ab initio conformational study of N-acetyl-L-proline-N',N'-dimethylamide: a model for polyproline.	2005-01-01	15617814
Chiral separation of NBD-amino acids by ligand-exchange micro-channel electrophoresis.	2005-01	15675519
Electronic structure of the nickel(II) complex of the Schiff base of (S)-N-(2-benzoylphenyl)-1-benzylprolinamide and glycine.	2004-09	15477692
S-stereoselective piperazine-2-tert-butylcarboxamide hydrolase from Pseudomonas azotoformans IAM 1603 is a novel L-amino acid amidase.	2004-04	15066172
Factors affecting conformation in proline-containing peptides.	2003-11-13	14602013
(+/-)-5-(4-methoxyphenylaminocarbonyl)-1-azabicyclo[3.3.0]octan-2-one benzene solvate.	2003-05	12743400
The mechanism of cis-trans isomerization of prolyl peptides by cyclophilin.	2002-06-26	12071739
Effect of sequence on peptide geometry in 5-tert-butylprolyl type VI beta-turn mimics.	2002-03-20	11890796
Chemically L-prolinamide-modified monolithic silica column for enantiomeric separation of dansyl amino acids and hydroxy acids by capillary electrochromatography and mu-high performance liquid chromatography.	2001-09	11589299
The influence of steric interactions on the conformation and biology of oxytocin. Synthesis and analysis of penicillamine(6)-oxytocin and penicillamine(6)-5-tert-butylproline(7)-oxytocin analogs.	2001-09	11576333
Influence of N-terminal residue stereochemistry on the prolyl amide geometry and the conformation of 5-tert-butylproline type VI beta-turn mimics.	2001-02	11277501

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 22:01:04 GMT 2025` Edited by `admin` on `Mon Mar 31 22:01:04 GMT 2025`
Record UNII	VD6PQK9DHG
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PROLINAMIDE

Systematic Name

English

(S)-PROLINE AMIDE

Preferred Name

English

S)-PYRROLIDINE-2-CARBOXYLIC ACID AMIDE

Common Name

English

PROLINAMIDE, L-

Systematic Name

English

(S)-PROLINAMIDE

Systematic Name

English

2-PYRROLIDINECARBOXAMIDE, (2S)-

Systematic Name

English

(S)-PYRROLIDINE-2-CARBOXAMIDE

Systematic Name

English

L-PROLINAMIDE

Systematic Name

English

PROLINE AMIDE

Common Name

English

L-PROLINE AMIDE

Common Name

English

Code System Code Type Description

ECHA (EC/EINECS)

231-397-0