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D4893

Sigma-Aldrich

3,4-Dehydro-L-proline

≥98% (TLC), suitable for ligand binding assays

Synonym(s):

(S)-3-Pyrroline-2-carboxylic acid, 3,4-Didehydro-L-proline

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About This Item

Empirical Formula (Hill Notation):
C5H7NO2
CAS Number:
4043-88-3
Molecular Weight:
113.11
Beilstein:
5376764
EC Number:
223-738-7
MDL number:
MFCD00065964
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
24893903
NACRES:
NA.26

product name

3,4-Dehydro-L-proline,

Assay

≥98% (TLC)

form

powder

technique(s)

ligand binding assay: suitable

color

white

mp

248-250 °C

application(s)

peptide synthesis

SMILES string

OC(=O)[C@H]1NCC=C1

InChI

1S/C5H7NO2/c7-5(8)4-2-1-3-6-4/h1-2,4,6H,3H2,(H,7,8)/t4-/m0/s1

InChI key

OMGHIGVFLOPEHJ-BYPYZUCNSA-N

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General description

3,4-Dehydro-L-proline acts a prolyl-t-RNA synthetase.

Biochem/physiol Actions

3,4-Dehydro-L-proline is used as a substrate and inhibitor of various enzymes. 3,4-Dehydro-L-proline may be used to inhibit extensin biosynthesis. 3,4-Dehydro-L-proline is a alternate substrate of the amino acid oxidase, NikD. 3,4-Dehydro-L-proline inhibits collagen secretion by chondorcytes.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Acute respiratory failure (1985)
Chunxiang Xu et al.
BMC plant biology, 11, 38-38 (2011-02-26)
Hydroxyproline rich glycoproteins (HRGPs) are implicated to have a role in many aspects of plant growth and development but there is limited knowledge about their localization and function during somatic embryogenesis of higher plants. In this study, the localization and
Annick Méjean et al.
Biochemistry, 49(1), 103-113 (2009-12-04)
Anatoxin-a and homoanatoxin-a are two potent cyanobacterial neurotoxins. We recently reported the identification of the gene cluster responsible for the biosynthesis of these toxins in cyanobacteria and proposed a biosynthetic scheme starting from L-proline and involving three polyketide synthases for
Richard C D'Alonzo et al.
The Journal of biological chemistry, 277(27), 24788-24798 (2002-04-20)
Both collagenase-3 and osteocalcin mRNAs are expressed maximally during the later stages of osteoblast differentiation. Here, we demonstrate that collagenase-3 mRNA expression in differentiating MC3T3-E1 cells is dependent upon the presence of ascorbic acid, is inhibited in the presence of
G Xiao et al.
Molecular endocrinology (Baltimore, Md.), 11(8), 1103-1113 (1997-07-01)
Osteocalcin is a hormonally regulated calcium-binding protein made almost exclusively by osteoblasts. In normal cells, osteocalcin expression requires ascorbic acid (AA), an essential cofactor for osteoblast differentiation both in vivo and in vitro. To determine the mechanism of this regulation
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