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H54409

Sigma-Aldrich

trans-4-Hydroxy-L-proline

≥99%, for peptide synthesis

Synonym(s):

(2S,4R)-4-Hydroxypyrrolidine-2-carboxylic acid, Hyp

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About This Item

Empirical Formula (Hill Notation):
C5H9NO3
CAS Number:
Molecular Weight:
131.13
Beilstein/REAXYS Number:
81441
EC Number:
MDL number:
UNSPSC Code:
12352209
PubChem Substance ID:
NACRES:
NA.22

product name

trans-4-Hydroxy-L-proline, ≥99%

Quality Level

assay

≥99%

form

crystalline powder

optical activity

[α]25/D −75.6°, c = 1 in H2O

reaction suitability

reaction type: solution phase peptide synthesis

color

white to off-white

mp

273 °C (dec.) (lit.)

application(s)

peptide synthesis

SMILES string

O[C@H]1CN[C@@H](C1)C(O)=O

InChI

1S/C5H9NO3/c7-3-1-4(5(8)9)6-2-3/h3-4,6-7H,1-2H2,(H,8,9)/t3-,4+/m1/s1

InChI key

PMMYEEVYMWASQN-DMTCNVIQSA-N

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General description

Trans-4-hydroxy-L-proline is an isomer of hydroxyproline used as a chiral building block in the production of many pharmaceuticals like neuroexcitatory kainoids.

Application

Versatile reagent for the synthesis of neuroexcitatory kainoids and antifungal echinocandins. Also employed in the synthesis of chiral ligands for enantioselective ethylation of aldehydes.

Other Notes

Natural constituent of animal structural proteins such as collagen and elastin.

wgk_germany

WGK 1

ppe

Eyeshields, Gloves, type N95 (US)


Certificates of Analysis (COA)

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Synthetic Communications, 23, 2691-2691 (1993)
Tetrahedron, 49, 6195-6195 (1993)
Biosynthesis of trans-4-hydroxyproline by recombinant strains of Corynebacterium glutamicum and Escherichia coli
Yi Y, et al.
BMC biotechnology, 14, 1-8 (2014)
Tetrahedron Letters, 35, 6163-6163 (1994)
Shahrzad Hosseininia et al.
BMC musculoskeletal disorders, 14, 18-18 (2013-01-11)
It remains to be shown whether OA shares molecular similarities between different joints in humans. This study provides evidence for similarities in cartilage molecular damage in osteoarthritic (OA) joints. Articular cartilage from osteoarthritic hip joints were analysed and compared to

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