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Application Area

Osteocalcin fragment 1-49 Human

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

Category

Peptide APIs

Catalog number

BAT-015235

CAS number

136461-80-8

Molecular Formula

C269H381N67O82S2

Molecular Weight

5929.43

Specification
Reference Reading

IUPAC Name

2-[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-1-[(2S)-2-[[(2S)-2-[[(2S)-1-[(2S)-2-[[(2S)-1-[(2S)-2-[[(2S)-1-[(2S)-2-[[(2S)-1-[(2S)-2-[[2-[[(2S)-2-[[(2S)-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]-4-methylpentanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-5-oxopentanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-4-methylpentanoyl]amino]acetyl]amino]propanoyl]pyrrolidine-2-carbonyl]amino]-3-methylbutanoyl]pyrrolidine-2-carbonyl]amino]-3-(4-hydroxyphenyl)propanoyl]pyrrolidine-2-carbonyl]amino]-3-carboxypropanoyl]pyrrolidine-2-carbonyl]amino]-4-methylpentanoyl]amino]-4,4-dicarboxybutanoyl]pyrrolidine-2-carbonyl]amino]-5-carbamimidamidopentanoyl]amino]-5-carbamimidamidopentanoyl]amino]-3-[[(2S)-1-[[(3S,6S,9S,12R,17R,20S,23S)-17-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S,3S)-1-[[2-[[(2S)-1-[[(2S)-5-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-5-carbamimidamido-1-[[(2S)-5-carbamimidamido-1-[[(2S)-1-[[(2S)-1-[[2-[(2S)-2-[[(1S)-1-carboxy-2-methylpropyl]carbamoyl]pyrrolidin-1-yl]-2-oxoethyl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-1-oxopentan-2-yl]amino]-1-oxopentan-2-yl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]amino]-4-carboxy-1-oxobutan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-2-oxoethyl]amino]-3-methyl-1-oxopentan-2-yl]amino]-3-(1H-imidazol-4-yl)-1-oxopropan-2-yl]amino]-3-carboxy-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-4-carboxy-1-oxobutan-2-yl]amino]-3-carboxy-1-oxopropan-2-yl]carbamoyl]-3-(2-amino-2-oxoethyl)-20-(carboxymethyl)-9-(2,2-dicarboxyethyl)-6-(2-methylpropyl)-2,5,8,11,19,22-hexaoxo-14,15-dithia-1,4,7,10,18,21-hexazabicyclo[21.3.0]hexacosan-12-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-3-oxopropyl]propanedioic acid

Synonyms

Osteocalcin (1-49) (human); H-Tyr-Leu-Tyr-Gln-Trp-Leu-Gly-Ala-Pro-Val-Pro-Tyr-Pro-Asp-Pro-Leu-Gla-Pro-Arg-Arg-Gla-Val-Cys-Gla-Leu-Asn-Pro-Asp-Cys-Asp-Glu-Leu-Ala-Asp-His-Ile-Gly-Phe-Gln-Glu-Ala-Tyr-Arg-Arg-Phe-Tyr-Gly-Pro-Val-OH (Disulfide bridge: Cys23-Cys29); L-tyrosyl-L-leucyl-L-tyrosyl-L-glutaminyl-L-tryptophyl-L-leucyl-glycyl-L-alanyl-L-prolyl-L-valyl-L-prolyl-L-tyrosyl-L-prolyl-L-alpha-aspartyl-L-prolyl-L-leucyl-gamma-carboxy-L-alpha-glutamyl-L-prolyl-L-arginyl-L-arginyl-gamma-carboxy-L-alpha-glutamyl-L-valyl-L-cysteinyl-gamma-carboxy-L-alpha-glutamyl-L-leucyl-L-asparagyl-L-prolyl-L-alpha-aspartyl-L-cysteinyl-L-alpha-aspartyl-L-alpha-glutamyl-L-leucyl-L-alanyl-L-alpha-aspartyl-L-histidyl-L-isoleucyl-glycyl-L-phenylalanyl-L-glutaminyl-L-alpha-glutamyl-L-alanyl-L-tyrosyl-L-arginyl-L-arginyl-L-phenylalanyl-L-tyrosyl-glycyl-L-prolyl-L-valine (23->29)-disulfide

Appearance

White Solid

Purity

≥90%

Sequence

YLYQWLGAPVPYPDPLXPRRXVCXLNPDCDELADHIGFQEAYRRFYGPV (Disulfide bridge: Cys23-Cys29)

Storage

Store at -80°C

InChI

InChI=1S/C269H381N67O82S2/c1-22-136(18)213(251(397)289-123-202(346)295-174(104-140-42-25-23-26-43-140)231(377)300-164(79-83-198(271)342)224(370)299-166(81-85-204(348)349)219(365)293-137(19)214(360)304-175(107-144-63-73-151(339)74-64-144)232(378)298-160(48-31-87-283-266(274)275)220(366)296-161(49-32-88-284-267(276)277)222(368)311-176(105-141-44-27-24-28-45-141)234(380)310-173(106-143-61-71-150(338)72-62-143)218(364)290-124-203(347)330-91-35-52-191(330)249(395)328-212(135(16)17)265(417)418)329-240(386)179(111-148-121-282-127-291-148)314-238(384)182(116-206(352)353)305-215(361)138(20)294-227(373)169(99-129(4)5)308-226(372)167(82-86-205(350)351)302-237(383)183(117-207(354)355)317-242(388)189-125-419-420-126-190(243(389)316-180(112-155(259(405)406)260(407)408)236(382)309-171(101-131(8)9)229(375)321-187(115-200(273)344)256(402)334-95-38-55-194(334)246(392)319-184(118-208(356)357)239(385)324-189)325-252(398)210(133(12)13)326-241(387)181(113-156(261(409)410)262(411)412)315-223(369)162(50-33-89-285-268(278)279)297-221(367)163(51-34-90-286-269(280)281)303-244(390)192-53-37-94-333(192)255(401)186(114-157(263(413)414)264(415)416)320-230(376)172(102-132(10)11)318-245(391)193-54-39-96-335(193)257(403)188(119-209(358)359)323-247(393)195-56-40-93-332(195)254(400)185(109-146-67-77-153(341)78-68-146)322-248(394)196-57-41-97-336(196)258(404)211(134(14)15)327-250(396)197-58-36-92-331(197)253(399)139(21)292-201(345)122-288-217(363)168(98-128(2)3)307-235(381)178(110-147-120-287-159-47-30-29-46-154(147)159)313-225(371)165(80-84-199(272)343)301-233(379)177(108-145-65-75-152(340)76-66-145)312-228(374)170(100-130(6)7)306-216(362)158(270)103-142-59-69-149(337)70-60-142/h23-30,42-47,59-78,120-121,127-139,155-158,160-197,210-213,287,337-341H,22,31-41,48-58,79-119,122-126,270H2,1-21H3,(H2,271,342)(H2,272,343)(H2,273,344)(H,282,291)(H,288,363)(H,289,397)(H,290,364)(H,292,345)(H,293,365)(H,294,373)(H,295,346)(H,296,366)(H,297,367)(H,298,378)(H,299,370)(H,300,377)(H,301,379)(H,302,383)(H,303,390)(H,304,360)(H,305,361)(H,306,362)(H,307,381)(H,308,372)(H,309,382)(H,310,380)(H,311,368)(H,312,374)(H,313,371)(H,314,384)(H,315,369)(H,316,389)(H,317,388)(H,318,391)(H,319,392)(H,320,376)(H,321,375)(H,322,394)(H,323,393)(H,324,385)(H,325,398)(H,326,387)(H,327,396)(H,328,395)(H,329,386)(H,348,349)(H,350,351)(H,352,353)(H,354,355)(H,356,357)(H,358,359)(H,405,406)(H,407,408)(H,409,410)(H,411,412)(H,413,414)(H,415,416)(H,417,418)(H4,274,275,283)(H4,276,277,284)(H4,278,279,285)(H4,280,281,286)/t136-,137-,138-,139-,158-,160-,161-,162-,163-,164-,165-,166-,167-,168-,169-,170-,171-,172-,173-,174-,175-,176-,177-,178-,179-,180-,181-,182-,183-,184-,185-,186-,187-,188-,189-,190-,191-,192-,193-,194-,195-,196-,197-,210-,211-,212-,213-/m0/s1

InChI Key

RIIWDESPKPBKFU-RTUNGCTQSA-N

Canonical SMILES

CCC(C)C(C(=O)NCC(=O)NC(CC1=CC=CC=C1)C(=O)NC(CCC(=O)N)C(=O)NC(CCC(=O)O)C(=O)NC(C)C(=O)NC(CC2=CC=C(C=C2)O)C(=O)NC(CCCNC(=N)N)C(=O)NC(CCCNC(=N)N)C(=O)NC(CC3=CC=CC=C3)C(=O)NC(CC4=CC=C(C=C4)O)C(=O)NCC(=O)N5CCCC5C(=O)NC(C(C)C)C(=O)O)NC(=O)C(CC6=CNC=N6)NC(=O)C(CC(=O)O)NC(=O)C(C)NC(=O)C(CC(C)C)NC(=O)C(CCC(=O)O)NC(=O)C(CC(=O)O)NC(=O)C7CSSCC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N8CCCC8C(=O)NC(C(=O)N7)CC(=O)O)CC(=O)N)CC(C)C)CC(C(=O)O)C(=O)O)NC(=O)C(C(C)C)NC(=O)C(CC(C(=O)O)C(=O)O)NC(=O)C(CCCNC(=N)N)NC(=O)C(CCCNC(=N)N)NC(=O)C9CCCN9C(=O)C(CC(C(=O)O)C(=O)O)NC(=O)C(CC(C)C)NC(=O)C1CCCN1C(=O)C(CC(=O)O)NC(=O)C1CCCN1C(=O)C(CC1=CC=C(C=C1)O)NC(=O)C1CCCN1C(=O)C(C(C)C)NC(=O)C1CCCN1C(=O)C(C)NC(=O)CNC(=O)C(CC(C)C)NC(=O)C(CC1=CNC2=CC=CC=C21)NC(=O)C(CCC(=O)N)NC(=O)C(CC1=CC=C(C=C1)O)NC(=O)C(CC(C)C)NC(=O)C(CC1=CC=C(C=C1)O)N

1. A meta-analysis of serum osteocalcin level in postmenopausal osteoporotic women compared to controls

Zhongyu Liu, Ruiqiang Chen, Yutong Jiang, Yang Yang, Lei He, Chunxiao Luo, Jianwen Dong, Limin Rong BMC Musculoskelet Disord. 2019 Nov 13;20(1):532. doi: 10.1186/s12891-019-2863-y.

Background: Circulatory osteocalcin (OC) has been widely used as a biomarker to indicate bone turnover status in postmenopausal osteoporosis (PMO). However, the change of serum OC (sOC) level in PMO cases compared to postmenopausal controls remains controversial. Methods: We searched the online database of PubMed and Cochrane Library. A meta-analysis of case-control studies was performed to compare the pooled sOC level between PMO patients and postmenopausal controls. Subgroup analysis according to potential confounding factors (different OC molecules and regions of the study population) was also performed. Results: Ten case-control studies with 1577 postmenopausal women were included in this meta analysis. We found no significant difference in the pooled sOC level [mean difference (MD) = 1.84, 95% confidence interval (CI): (- 1.49, 5.16), p = 0.28] between PMO patients and controls. Subgroup analysis also revealed no significant difference in intact OC [MD = 1.76, 95%CI: (- 1.71, 5.23), p = 0.32] or N-terminal mid-fragment of the OC molecule [MD = 0.67, 95%(- 5.83, 7.18), p = 0.84] between groups. For different regions, no significant difference in sOC was found in Asian population between cases and controls [MD = -0.06, 95%(- 6.02, 5.89), p = 0.98], while the pooled sOC level was significantly higher in European PMO cases than controls [MD = 3.15, 95%(0.90, 5.39), p = 0.006]. Conclusions: Our analysis revealed no significant difference in sOC level between PMO cases and controls according to all the current eligible studies. OC molecules are quite heterogeneous in the circulation and can be influenced by glucose metabolism. Therefore, sOC is currently not a good indicator for the high bone turnover status in PMO. More trials with standardized methodologies for the evaluation of circulatory OC are awaited to update our current findings.

2. Immunoradiometric assay for intact human osteocalcin(1-49) without cross-reactivity to breakdown products

J W Colford, B A Lueddecke, M Salvati, D Hanna, D Sailer, S Khosla, B L Riggs, C B Langman Clin Chem. 1999 Apr;45(4):526-31.

Background: Osteocalcin (Oc), a serum marker of bone turnover, circulates in several forms. We developed an assay for intact human Oc and investigated its clinical features. Methods: We generated goat antibodies and N- and C-terminal Oc. The former was used on solid phase (polystyrene beads), and the latter was used as the tracer in an IRMA. Results: The assay was linear with no cross-reactivity to Oc(1-43), total imprecision (CV) of <10%, and recovery of 100% +/- 10%. Assay values for intact Oc in EDTA plasma samples were unchanged at 18-25 degrees C for 6 h. Values for intact Oc in serum, EDTA plasma, and heparin plasma samples did not change after storage on ice for 8 h. Serum samples from patients with various conditions were stored at -70 or -135 degrees C for up to 5 years and yielded z-scores comparable to an Oc(1-43) IRMA for all conditions except for renal failure. In renal failure, the Oc(1-43) assay values were increased, whereas the intact assay values were in the reference interval. Conclusion: Decreases in Oc assay values are inhibited by calcium chelation, and slowed by reduced temperatures. The described assay for intact Oc allows improved specificity for bone compared with an assay for Oc(1-43).

3. Association of bone turnover markers with mortality in men referred to coronary angiography

E Lerchbaum, V Schwetz, S Pilz, T B Grammer, M Look, B O Boehm, B Obermayer-Pietsch, W März Osteoporos Int. 2013 Apr;24(4):1321-32. doi: 10.1007/s00198-012-2076-9. Epub 2012 Jul 10.

We aimed to examine the association of fatal events with osteocalcin (OC) and beta-crosslaps (β-CTX) levels in men. We observed a U-shaped association of OC and β-CTX levels with fatal events in a large cohort of men at high cardiovascular risk. Introduction: Accumulating evidence suggests an association of low OC levels with metabolic disturbances. Whether OC levels are related to fatal events is, however, less clear. Further, high β-CTX levels are linked to increased mortality. We aimed to examine the association of fatal events with both OC and β-CTX in men. Methods: We measured OC and β-CTX in 2,271 men referred to coronary angiography (1997-2000). Results: We observed a U-shaped association of OC and β-CTX with fatal events. Crude hazard ratios (HRs) for all-cause and non-cardiovascular mortality in the highest OC quintile were 1.38 (1.04-1.83) and 1.47 (0.89-2.40), respectively, and 2.11 (1.61-2.75) and 2.06 (1.29-3.29) for men in the lowest compared to the third OC quintile. In multivariate-adjusted models, HRs for all-cause, and non-cardiovascular mortality in the lowest OC quintile were 1.63 (1.23-2.16) and 1.79 (1.10-2.92), respectively, compared to the third OC quintile, whereas the association of high OC with mortality lost its significance. Crude and multivariate-adjusted HRs for cardiovascular mortality in the lowest OC quintile compared to the third OC quintile were 2.08 (1.49-2.90) and 1.74 (1.24-2.46), respectively. Moreover, high as well as low β-CTX levels were independently associated with all-cause (quintile 1 vs. quintile 3: HR 1.42 (1.05-1.92); quintile 5 vs. quintile 3: HR 1.79 (1.31-2.45)) and cardiovascular mortality (quintile 1 vs. quintile 3: HR 1.55 (1.05-2.28); quintile 5 vs. quintile 3: HR 1.85 (1.23-2.77)). Conclusions: We observed a U-shaped association of OC and β-CTX with fatal events in a large cohort of men at high cardiovascular risk.