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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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2.5 G
CHF 35.60
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CHF 77.40
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CHF 203.00

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Estimated to ship on27 March 2025


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2.5 G
CHF 35.60
10 G
CHF 58.00
25 G
CHF 77.40
100 G
CHF 203.00

About This Item

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

CHF 35.60


Estimated to ship on27 March 2025


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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.[1]

Application

Versatile reagent for the synthesis of neuroexcitatory kainoids[2] and antifungal echinocandins.[3] Also employed in the synthesis of chiral ligands for enantioselective ethylation of aldehydes.[4]

Other Notes

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Tetrahedron Letters, 35, 6163-6163 (1994)
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, 49, 6195-6195 (1993)
Synthetic Communications, 23, 2691-2691 (1993)
Stefan de Vries et al.
Tissue engineering. Part A, 25(11-12), 830-841 (2018-05-10)
Notochordal cells (NCs) reside in the core of the healthy disc and produce soluble factors that can stimulate nucleus pulposus cells (NPCs). These NC-derived factors may be applied in intervertebral disc regeneration for treatment of low-back pain. However, identification of

Questions

  1. Guten Tag, ist der Stoff zur äußerlichen und innerlichen Anwendung geeignet?

    1 answer
    1. Unless otherwise stated this product is intended for research use only and is not to be used for any other purpose, which includes but is not limited to, unauthorized commercial uses, in vitro diagnostic uses, ex vivo or in vivo therapeutic uses, or any type of consumption or application to humans or animals.

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